3-ethyl-3-phenylpiperidine-2,6-dione (Glutethimide) by Asch

Query Query

Results

Date

42 reactions in Reaxys

2016-06-01 21h:25m:34s (EST)

O HN O

1. Query

Search as: As drawn

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NH N

Rx-ID: 9408977 View in Reaxys 1/42 Yield

Conditions & References

92 %

With IrH5(P-i-Pr3)2, water in tetrahydrofuran, Time= 30h, T= 180 °C Takaya, Hikaru; Yoshida, Kazunori; Isozaki, Katsuhiro; Terai, Hiroki; Murahashi, Shun-Ichi; Angewandte Chemie - International Edition; vol. 42; nb. 28; (2003); p. 3302 - 3304 View in Reaxys

O O

O OH

Rx-ID: 4278602 View in Reaxys 2/42 Yield

Conditions & References

81 %

With ammonium hydroxide, Time= 1h, T= 180 - 200 °C Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O NH

NH O

Rx-ID: 1930394 View in Reaxys 3/42 Yield

Conditions & References in propan-1-ol, 1,2-dichloro-ethane, T= 25 °C , HPLC chiral separation by derivative of N,N'-2,6-pyridinediylbis<(S)-2-phenylbutanamide> Feibush; Figueroa; Charles; et al.; Journal of the American Chemical Society; vol. 108; nb. 12; (1986); p. 3310 3318 View in Reaxys Blaschke, Gottfried; Kraft, Horst Peter; Markgraf, Hildegunde; Chemische Berichte; vol. 116; nb. 11; (1983); p. 3611 - 3617 View in Reaxys

O O

NH O

Rx-ID: 4492291 View in Reaxys 4/42 Yield 83 %

Conditions & References With ammonium hydroxide, Time= 4h, T= 170 - 180 °C Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 2 1: 100 percent / aq. NaOH / ethanol / 10 h / Heating

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2: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With ammonium hydroxide, sodium hydroxide in ethanol Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

N O NH

HO O

Rx-ID: 312016 View in Reaxys 5/42 Yield

Conditions & References

70 %

With sulfuric acid in toluene, Time= 4h, Inert atmosphere, Reflux Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 - 946 View in Reaxys With sulfuric acid, acetic acid Tagmann et al.; Helvetica Chimica Acta; vol. 35; (1952); p. 1541,1545 View in Reaxys Salmon-Legagneur; Neveu; Bulletin de la Societe Chimique de France; (1953); p. 70,74 View in Reaxys

OH O

NH O

Rx-ID: 4490268 View in Reaxys 6/42 Yield

Conditions & References

79 %

With ammonium hydroxide, Time= 4h, T= 180 - 200 °C Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O N

NH O

Rx-ID: 8683352 View in Reaxys 7/42 Yield

Conditions & References

82 %

With aluminium trichloride in benzene, Heating Chang, Meng-Yang; Chang, Bo-Rui; Tai, Huo-Mu; Chang, Nein-Chen; Tetrahedron Letters; vol. 41; nb. 52; (2000); p. 10273 - 10276 View in Reaxys

O NH

NH O

Rx-ID: 1930391 View in Reaxys 8/42

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Yield

O NH

NH O

Rx-ID: 4988571 View in Reaxys 9/42 Yield

Conditions & References Schleuder; Duerrbeck; Jira; Pharmazie; vol. 53; nb. 6; (1998); p. 381 - 386 View in Reaxys Patent; Novartis AG; Novartis Pharma GmbH; EP907663; (2004); (B1) English View in Reaxys With chiral stationary phase derived from aminated silica gel, (1S,2R)-1,2-diphenyl-2-(3-phenylureido)ethyl 4-isocyanatophenylcarbamate and three-generation dendrimer in water, acetonitrile, T= 25 °C , Resolution of racemate He, Bao-Jiang; Yin, Chuan-Qi; Li, Shi-Rong; Bai, Zheng-Wu; Chirality; vol. 22; nb. 1; (2010); p. 69 - 76 View in Reaxys With tetraproline chiral stationary phase packed on HPLC column in hexane, isopropyl alcohol, Resolution of racemate Dai, Zhi; Ye, Guozhong; Pittman Jr., Charles U.; Li, Tingyu; Chirality; vol. 24; nb. 4; (2012); p. 329 - 338 View in Reaxys

O O

Rx-ID: 17714910 View in Reaxys 10/42 Yield

Conditions & References Reaction Steps: 8 1: SOCl2, MgSO4 / 10 h / 50 °C 2: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 3: Et3N / tetrahydrofuran / 0.25 h / -15 °C 4: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 6: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 7: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 8: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, thionyl chloride, oxalyl dichloride, hydrogen, magnesium sulfate, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 9 1: SOCl2, MgSO4 / 10 h / 50 °C 2: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 3: Et3N / tetrahydrofuran / 0.25 h / -15 °C

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4: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 6: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 7: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 8: 100 percent / aq. NaOH / ethanol / 10 h / Heating 9: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, thionyl chloride, oxalyl dichloride, hydrogen, magnesium sulfate, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 8 1: SOCl2, MgSO4 / 10 h / 50 °C 2: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 3: (COCl)2, DMF / CH2Cl2 / 2 h / Ambient temperature 4: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 6: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 7: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 8: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, thionyl chloride, oxalyl dichloride, hydrogen, magnesium sulfate, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, N,N-dimethylformamide, lithium chloride, platinum(IV) oxide in tetrahydrofuran, dichloromethane, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 9 1: SOCl2, MgSO4 / 10 h / 50 °C 2: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 3: (COCl)2, DMF / CH2Cl2 / 2 h / Ambient temperature 4: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 6: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 7: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 8: 100 percent / aq. NaOH / ethanol / 10 h / Heating 9: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, thionyl chloride, oxalyl dichloride, hydrogen, magnesium sulfate, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, N,N-dimethylformamide, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, dichloromethane, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O HO

O NH

HO O

Rx-ID: 17715430 View in Reaxys 11/42 Yield

Conditions & References Reaction Steps: 9 1: 1.) BuLi 2: SOCl2, MgSO4 / 10 h / 50 °C 3: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 4: Et3N / tetrahydrofuran / 0.25 h / -15 °C 5: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C

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6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 7: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 8: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 9: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, n-butyllithium, thionyl chloride, oxalyl dichloride, hydrogen, magnesium sulfate, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 10 1: 1.) BuLi 2: SOCl2, MgSO4 / 10 h / 50 °C 3: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 4: Et3N / tetrahydrofuran / 0.25 h / -15 °C 5: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 7: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 8: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 9: 100 percent / aq. NaOH / ethanol / 10 h / Heating 10: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, n-butyllithium, thionyl chloride, oxalyl dichloride, hydrogen, magnesium sulfate, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 9 1: 1.) BuLi 2: SOCl2, MgSO4 / 10 h / 50 °C 3: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 4: (COCl)2, DMF / CH2Cl2 / 2 h / Ambient temperature 5: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 7: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 8: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 9: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, n-butyllithium, thionyl chloride, oxalyl dichloride, hydrogen, magnesium sulfate, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, N,N-dimethyl-formamide, lithium chloride, platinum(IV) oxide in tetrahydrofuran, dichloromethane, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 10 1: 1.) BuLi 2: SOCl2, MgSO4 / 10 h / 50 °C 3: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 4: (COCl)2, DMF / CH2Cl2 / 2 h / Ambient temperature 5: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 7: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 8: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 9: 100 percent / aq. NaOH / ethanol / 10 h / Heating 10: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, n-butyllithium, thionyl chloride, oxalyl dichloride, hydrogen, magnesium sulfate, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethyla-

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mine, N,N-dimethyl-formamide, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, dichloromethane, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O O

Rx-ID: 17717178 View in Reaxys 12/42 Yield

Conditions & References Reaction Steps: 7 1: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 2: Et3N / tetrahydrofuran / 0.25 h / -15 °C 3: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 5: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 6: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 7: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 8 1: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 2: Et3N / tetrahydrofuran / 0.25 h / -15 °C 3: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 5: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 6: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 7: 100 percent / aq. NaOH / ethanol / 10 h / Heating 8: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 7 1: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 2: (COCl)2, DMF / CH2Cl2 / 2 h / Ambient temperature 3: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 5: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 6: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 7: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, N,N-dimethyl-formamide, lithium chloride, platinum(IV) oxide in tetrahydrofuran, dichloromethane, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 8

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1: 75 percent / 2N aq. NaOH / 25 °C / pig liver esterase 2: (COCl)2, DMF / CH2Cl2 / 2 h / Ambient temperature 3: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 5: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 6: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 7: 100 percent / aq. NaOH / ethanol / 10 h / Heating 8: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, N,N-dimethyl-formamide, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, dichloromethane, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O O HO

NH O

Rx-ID: 17741496 View in Reaxys 13/42 Yield

Conditions & References Reaction Steps: 6 1: Et3N / tetrahydrofuran / 0.25 h / -15 °C 2: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 4: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 5: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 6: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 7 1: Et3N / tetrahydrofuran / 0.25 h / -15 °C 2: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 4: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 5: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 6: 100 percent / aq. NaOH / ethanol / 10 h / Heating 7: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 6 1: (COCl)2, DMF / CH2Cl2 / 2 h / Ambient temperature 2: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 4: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 5: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 6: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C

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With methanol, ammonium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8diazabicyclo[5.4.0]undec-7-ene, triethylamine, N,N-dimethyl-formamide, lithium chloride, platinum(IV) oxide in tetrahydrofuran, dichloromethane, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 7 1: (COCl)2, DMF / CH2Cl2 / 2 h / Ambient temperature 2: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 4: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 5: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 6: 100 percent / aq. NaOH / ethanol / 10 h / Heating 7: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, N,N-dimethyl-formamide, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, dichloromethane, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O O

O NH

Rx-ID: 17985083 View in Reaxys 14/42 Yield

Conditions & References Reaction Steps: 11 1: 20 percent / D-glucose, bakers' yeast / aq. ethanol / 16 h / 23 °C / bakers' yeastY 2: 76 percent / LiBH4 / tetrahydrofuran / 5 - 10 °C 3: 73 percent / H5IO6 / tetrahydrofuran / 0.17 h 4: 75 percent / CHCl3 / 1 h / Ambient temperature 5: H2 / 5percent Pd/C / ethanol 6: HCl / ethanol 7: 73 percent / PCC 8: 61 percent / Me3Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C 9: 95 percent / H2 / 5percent Pd/C / ethanol 10: 89 percent / aq. NaOH / ethanol / 4 h / Heating 11: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With hydrogenchloride, ammonium hydroxide, sodium hydroxide, lithium borohydride, D-glucose, bakers' yeast, hydrogen, trimethylaluminum, periodic acid, pyridinium chlorochromate, zinc, palladium on activated charcoal in tetrahydrofuran, ethanol, hexane, chloroform Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O O

Rx-ID: 17985304 View in Reaxys 15/42 Yield

Conditions & References Reaction Steps: 3 1: 95 percent / H2 / 5percent Pd/C / ethanol

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2: 89 percent / aq. NaOH / ethanol / 4 h / Heating 3: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With ammonium hydroxide, sodium hydroxide, hydrogen, palladium on activated charcoal in ethanol Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O O

Rx-ID: 17985494 View in Reaxys 16/42 Yield

Conditions & References Reaction Steps: 4 1: 61 percent / Me3Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C 2: 95 percent / H2 / 5percent Pd/C / ethanol 3: 89 percent / aq. NaOH / ethanol / 4 h / Heating 4: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With ammonium hydroxide, sodium hydroxide, hydrogen, trimethylaluminum, zinc, palladium on activated charcoal in tetrahydrofuran, ethanol, hexane Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O O

OH O

Rx-ID: 17985500 View in Reaxys 17/42 Yield

Conditions & References Reaction Steps: 5 1: 73 percent / PCC 2: 61 percent / Me3Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C 3: 95 percent / H2 / 5percent Pd/C / ethanol 4: 89 percent / aq. NaOH / ethanol / 4 h / Heating 5: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With ammonium hydroxide, sodium hydroxide, hydrogen, trimethylaluminum, pyridinium chlorochromate, zinc, palladium on activated charcoal in tetrahydrofuran, ethanol, hexane Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O O

O E

Rx-ID: 17985733 View in Reaxys 18/42 Yield

Conditions & References Reaction Steps: 7 1: H2 / 5percent Pd/C / ethanol 2: HCl / ethanol

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3: 73 percent / PCC 4: 61 percent / Me3Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C 5: 95 percent / H2 / 5percent Pd/C / ethanol 6: 89 percent / aq. NaOH / ethanol / 4 h / Heating 7: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With hydrogenchloride, ammonium hydroxide, sodium hydroxide, hydrogen, trimethylaluminum, pyridinium chlorochromate, zinc, palladium on activated charcoal in tetrahydrofuran, ethanol, hexane Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

Rx-ID: 17985740 View in Reaxys 19/42 Yield

Conditions & References Reaction Steps: 6 1: HCl / ethanol 2: 73 percent / PCC 3: 61 percent / Me3Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C 4: 95 percent / H2 / 5percent Pd/C / ethanol 5: 89 percent / aq. NaOH / ethanol / 4 h / Heating 6: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With hydrogenchloride, ammonium hydroxide, sodium hydroxide, hydrogen, trimethylaluminum, pyridinium chlorochromate, zinc, palladium on activated charcoal in tetrahydrofuran, ethanol, hexane Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O O

Rx-ID: 17988594 View in Reaxys 20/42 Yield

Conditions & References Reaction Steps: 8 1: 75 percent / CHCl3 / 1 h / Ambient temperature 2: H2 / 5percent Pd/C / ethanol 3: HCl / ethanol 4: 73 percent / PCC 5: 61 percent / Me3Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C 6: 95 percent / H2 / 5percent Pd/C / ethanol 7: 89 percent / aq. NaOH / ethanol / 4 h / Heating 8: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With hydrogenchloride, ammonium hydroxide, sodium hydroxide, hydrogen, trimethylaluminum, pyridinium chlorochromate, zinc, palladium on activated charcoal in tetrahydrofuran, ethanol, hexane, chloroform Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

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O OH

Rx-ID: 17988649 View in Reaxys 21/42 Yield

Conditions & References Reaction Steps: 9 1: 73 percent / H5IO6 / tetrahydrofuran / 0.17 h 2: 75 percent / CHCl3 / 1 h / Ambient temperature 3: H2 / 5percent Pd/C / ethanol 4: HCl / ethanol 5: 73 percent / PCC 6: 61 percent / Me3Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C 7: 95 percent / H2 / 5percent Pd/C / ethanol 8: 89 percent / aq. NaOH / ethanol / 4 h / Heating 9: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With hydrogenchloride, ammonium hydroxide, sodium hydroxide, hydrogen, trimethylaluminum, periodic acid, pyridinium chlorochromate, zinc, palladium on activated charcoal in tetrahydrofuran, ethanol, hexane, chloroform Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O O

Rx-ID: 17988661 View in Reaxys 22/42 Yield

Conditions & References Reaction Steps: 10 1: 76 percent / LiBH4 / tetrahydrofuran / 5 - 10 °C 2: 73 percent / H5IO6 / tetrahydrofuran / 0.17 h 3: 75 percent / CHCl3 / 1 h / Ambient temperature 4: H2 / 5percent Pd/C / ethanol 5: HCl / ethanol 6: 73 percent / PCC 7: 61 percent / Me3Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C 8: 95 percent / H2 / 5percent Pd/C / ethanol 9: 89 percent / aq. NaOH / ethanol / 4 h / Heating 10: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With hydrogenchloride, ammonium hydroxide, sodium hydroxide, lithium borohydride, hydrogen, trimethylaluminum, periodic acid, pyridinium chlorochromate, zinc, palladium on activated charcoal in tetrahydrofuran, ethanol, hexane, chloroform Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O H NH N

Rx-ID: 19031643 View in Reaxys 23/42 Yield

Conditions & References Reaction Steps: 2

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1: 53 percent / trimethylbenzylammoniumhydroxide (Triton B) / dioxane; methanol / 15 h / Heating 2: 59 percent / concd H2SO4, CH3CO2H / 6 h With sulfuric acid, N-benzyl-trimethylammonium hydroxide, acetic acid in 1,4-dioxane, methanol Hartmann, Rolf W.; Batzl, Christine; Journal of Medicinal Chemistry; vol. 29; nb. 8; (1986); p. 1362 - 1369 View in Reaxys Reaction Steps: 2 1: NaNH2 / anschliessend Umsetzung mit wss.-aethanol. KOH 2: acetic acid; sulfuric acid With sulfuric acid, sodium amide, acetic acid Salmon-Legagneur; Neveu; Bulletin de la Societe Chimique de France; (1953); p. 70,74 View in Reaxys Reaction Steps: 3 1: N-benzyl-trimethylammonium hydroxide / methanol; 1,4-dioxane / 3 h / 0 - 20 °C / |Inert atmosphere 2: sodium hydroxide / methanol; water / 3 h / 50 °C / |Inert atmosphere 3: sulfuric acid / toluene / 4 h / |Inert atmosphere; |Reflux With sulfuric acid, N-benzyl-trimethylammonium hydroxide, sodium hydroxide in 1,4-dioxane, methanol, water, toluene, 1: |Michael Addition Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 - 946 View in Reaxys

O O

Rx-ID: 17731430 View in Reaxys 24/42 Yield

Conditions & References Reaction Steps: 3 1: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 2: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 3: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With ammonium hydroxide, hydrogen, 1,8-diazabicyclo[5.4.0]undec-7-ene, lithium chloride, platinum(IV) oxide in ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 4 1: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 2: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 3: 100 percent / aq. NaOH / ethanol / 10 h / Heating 4: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With ammonium hydroxide, sodium hydroxide, hydrogen, 1,8-diazabicyclo[5.4.0]undec-7-ene, lithium chloride, platinum(IV) oxide in ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O O Cl

NH O

Rx-ID: 17732042 View in Reaxys 25/42

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Yield

Conditions & References Reaction Steps: 5 1: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 3: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 4: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 5: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 6 1: NaBH4, MeOH / tetrahydrofuran / 2 h / -30 - 20 °C 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 3: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 4: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 5: 100 percent / aq. NaOH / ethanol / 10 h / Heating 6: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O E

Rx-ID: 17734013 View in Reaxys 26/42 Yield

Conditions & References Reaction Steps: 2 1: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 2: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With ammonium hydroxide, hydrogen, platinum(IV) oxide in ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 3 1: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 2: 100 percent / aq. NaOH / ethanol / 10 h / Heating 3: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With ammonium hydroxide, sodium hydroxide, hydrogen, platinum(IV) oxide in ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O O

Rx-ID: 17735112 View in Reaxys 27/42

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Yield

Conditions & References Reaction Steps: 5 1: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 3: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 4: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 5: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With methanol, ammonium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 6 1: NaBH4, MeOH / tetrahydrofuran / 2 h / 0 °C 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 3: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 4: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 5: 100 percent / aq. NaOH / ethanol / 10 h / Heating 6: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With methanol, ammonium hydroxide, sodium hydroxide, sodium tetrahydroborate, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in tetrahydrofuran, ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

O O OH

NH O

Rx-ID: 17741378 View in Reaxys 28/42 Yield

Conditions & References Reaction Steps: 4 1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 2: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 3: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 4: 83 percent / 30percent aq. NH3 / 4 h / 170 - 180 °C With ammonium hydroxide, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys Reaction Steps: 5 1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C 2: 1.) LiCl, DBU / 1.) MeCN, RT, 1 h, 2.) MeCN, RT, 4 h 3: 95 percent / H2 / PtO2 / ethyl acetate / 20 h / 760 Torr / Ambient temperature 4: 100 percent / aq. NaOH / ethanol / 10 h / Heating 5: 79 percent / 30percent aq. NH3 / 4 h / 180 - 200 °C With ammonium hydroxide, sodium hydroxide, oxalyl dichloride, hydrogen, dimethyl sulfoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, triethylamine, lithium chloride, platinum(IV) oxide in ethanol, ethyl acetate Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166 View in Reaxys

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O NH N

Rx-ID: 2155794 View in Reaxys 29/42 Yield

Conditions & References

59 %

With sulfuric acid, acetic acid, Time= 6h Hartmann, Rolf W.; Batzl, Christine; Journal of Medicinal Chemistry; vol. 29; nb. 8; (1986); p. 1362 - 1369 View in Reaxys

phenylcyanopyruvic acid ethyl ester-phenylhydrazone of mp: 107-108 degree

NH O

Rx-ID: 19033528 View in Reaxys 30/42 Yield

Conditions & References Reaction Steps: 3 1: 73 percent / NaNH2 / benzene; toluene / 1 h / 80 °C 2: 53 percent / trimethylbenzylammoniumhydroxide (Triton B) / dioxane; methanol / 15 h / Heating 3: 59 percent / concd H2SO4, CH3CO2H / 6 h With sulfuric acid, N-benzyl-trimethylammonium hydroxide, sodium amide, acetic acid in 1,4-dioxane, methanol, toluene, benzene Hartmann, Rolf W.; Batzl, Christine; Journal of Medicinal Chemistry; vol. 29; nb. 8; (1986); p. 1362 - 1369 View in Reaxys

O O

Rx-ID: 17985318 View in Reaxys 31/42 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / aq. NaOH / ethanol / 4 h / Heating 2: 81 percent / 30percent NH3 / 1 h / 180 - 200 °C With ammonium hydroxide, sodium hydroxide in ethanol Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695 View in Reaxys

O NH

N O

Rx-ID: 4988570 View in Reaxys 32/42 Yield

Conditions & References With water-d2 in chloroform-d1, Time= 1h Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153 View in Reaxys

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Rx-ID: 42149508 View in Reaxys 33/42 Yield

Conditions & References Reaction Steps: 4 1: potassium carbonate / methanol; water / 1 h / 20 °C / |Inert atmosphere 2: N-benzyl-trimethylammonium hydroxide / methanol; 1,4-dioxane / 3 h / 0 - 20 °C / |Inert atmosphere 3: sodium hydroxide / methanol; water / 3 h / 50 °C / |Inert atmosphere 4: sulfuric acid / toluene / 4 h / |Inert atmosphere; |Reflux With sulfuric acid, N-benzyl-trimethylammonium hydroxide, potassium carbonate, sodium hydroxide in 1,4-dioxane, methanol, water, toluene, 2: |Michael Addition Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 - 946 View in Reaxys

O–

F F

I+

O NH

Rx-ID: 42149513 View in Reaxys 34/42 Yield

Conditions & References Reaction Steps: 5 1.1: potassium tert-butylate / dichloromethane / 0.08 h / 0 °C / |Inert atmosphere 1.2: 0.75 h / 0 °C / |Inert atmosphere 2.1: potassium carbonate / methanol; water / 1 h / 20 °C / |Inert atmosphere 3.1: N-benzyl-trimethylammonium hydroxide / methanol; 1,4-dioxane / 3 h / 0 - 20 °C / |Inert atmosphere 4.1: sodium hydroxide / methanol; water / 3 h / 50 °C / |Inert atmosphere 5.1: sulfuric acid / toluene / 4 h / |Inert atmosphere; |Reflux With sulfuric acid, potassium tert-butylate, N-benzyl-trimethylammonium hydroxide, potassium carbonate, sodium hydroxide in 1,4-dioxane, methanol, dichloromethane, water, toluene, 3.1: |Michael Addition Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 - 946 View in Reaxys

H 2N

NH 2

C O

Rx-ID: 30119730 View in Reaxys 35/42 Yield

Conditions & References With DMPO, dihydrogen peroxide, Myeloperoxidase, T= 37 °C , aq. buffer Siraki, Arno G.; Jiang, Jinjie; Mason, Ronald P.; Chemical Research in Toxicology; vol. 23; nb. 5; (2010); p. 880 887 View in Reaxys

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4-cyano-4-phenyl-hexanoic acid methyl ester

NH O

Rx-ID: 5709036 View in Reaxys 36/42 Yield

Conditions & References With sulfuric acid, acetic acid Bernhard et al.; Helvetica Chimica Acta; vol. 39; (1956); p. 596,603 View in Reaxys

O NH

NH O

Rx-ID: 223840 View in Reaxys 37/42 Yield

Conditions & References With ethanol, platinum, Hydrogenation Hoffmann et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 387,394 View in Reaxys

(R)-4-cyano-4-phenyl-hexanoic acid

NH O

Rx-ID: 5709035 View in Reaxys 38/42 Yield

Conditions & References With sulfuric acid, acetic acid Branchini et al.; Ricerca Scientifica; vol. 29; (1959); p. 2435 View in Reaxys

O NH O

Rx-ID: 22221098 View in Reaxys 39/42 Yield

Conditions & References Reaction Steps: 3 1: benzyl-trimethyl-ammonium hydroxide 2: acetic acid; water; sulfuric acid 3: platinum; ethanol / Hydrogenation With ethanol, sulfuric acid, water, N-benzyl-trimethylammonium hydroxide, acetic acid, platinum Hoffmann et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 387,394 View in Reaxys

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O NH N

Rx-ID: 22226288 View in Reaxys 40/42 Yield

Conditions & References Reaction Steps: 2 1: acetic acid; water; sulfuric acid 2: platinum; ethanol / Hydrogenation With ethanol, sulfuric acid, water, acetic acid, platinum Hoffmann et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 387,394 View in Reaxys

O NH O

Rx-ID: 5463591 View in Reaxys 41/42 Yield

Conditions & References Branchini et al.; Farmaco, Edizione Scientifica; vol. 15; (1960); p. 734,744, 745, 746, 756 View in Reaxys Patent; Lodzkie Zaklady Farmaceutyczne 'Polfa'; NL6405774; (1963); ; vol. 62; nb. 11743a; (1965) View in Reaxys Patent; Lodzkie Zaklady Farm. 'Polfa'; PL53907; (1965); ; vol. 68; nb. 77997s; (1968) View in Reaxys Patent; Pliva; NL283796; (1965); ; vol. 63; nb. 9881e; (1965) View in Reaxys Patent; Taisho Pharmaceutical Co., Ltd.; JP2084964; (1961); ; vol. 62; nb. 10384c; (1965) View in Reaxys Patent; Pakleppa; DD16295; (1959); ; vol. 55; nb. 575e; (1961) View in Reaxys Kukolja et al.; Croatica Chemica Acta; vol. 33; (1961); p. 41,42 View in Reaxys 2H

2H 2H O 2

H NH O

Rx-ID: 5993475 View in Reaxys 42/42 Yield

Conditions & References Nitril (2), HOAc, H2SO4 Aboul-Enein; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 13; (1977); p. 509,510,512 View in Reaxys

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