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18 reactions in Reaxys
2016-05-23 23h:03m:53s (EST)
O
1. Query NH 2
Search as: As drawn
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O
O
O
N
H 2N
O
Rx-ID: 9826222 View in Reaxys 1/18 Yield
Conditions & References
68 %
With hydrazine in ethanol, Time= 1h, T= 40 °C Bertz, Steven H.; Ogle, Craig A.; Rastogi, Abhinav; Journal of the American Chemical Society; vol. 127; nb. 5; (2005); p. 1372 - 1373 View in Reaxys
O
O
O N
H 2N
O
Rx-ID: 467711 View in Reaxys 2/18 Yield
Conditions & References With lithium aluminium tetrahydride Tachikawa; Tetrahedron; vol. 7; (1959); p. 118,122 View in Reaxys With formic acid, coppered zinc, die konfigurative Einheitlichkeit des Praeparats ist ungewiss Patent; Merck,E.; DE556709; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 1114 View in Reaxys
3.6 g
With hydrogen, nickel in ethanol, Time= 48h, p= 53200Torr , Ambient temperature Ardabilchi, Nasser; Fitton, Alan O.; Hadi, A. Hamid b. A.; Thompson, J. Robin; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1710 - 1725 View in Reaxys With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, Heating Osorio-Olivares, Mauricio; Rezende, Marcos Caroli; Sepulveda-Boza, Silvia; Cassels, Bruce K.; Fierro, Angelica; Bioorganic and Medicinal Chemistry; vol. 12; nb. 15; (2004); p. 4055 - 4066 View in Reaxys
O HO
HN transtrans transtrans
erythro erythro NH 2
Rx-ID: 40479726 View in Reaxys 3/18 Yield 33 mg
Conditions & References ery? zro-l-Methoxy-l-phenylpropan-2-amine: CSA (46 mg, 0.2 mmol) was added to a stirring 0 °C solution of (is)-2-methyl-3-phenylaziridine 12c (27 mg, 0.2 mmol) in dry MeOH (2 mL). After 1 h, the reaction mixture was warmed to rt. After 16 h, the reaction mixture was warmed to 40 °C and held at this temperature for an additional 1 h. The reaction mixture was then cooled to rt, diluted with CHCI3 (5 mL), and the pH was adjusted to 8.5 using aqueous 1.0 M NaOH. The layers were separated, and the aqueous layer was extracted with CHCI3 (5 m x 3). The combined organic layers were washed with brine (5 mL), dried over Na2S04, and concentrated to obtain the title amino-alcohol as a light yellow oil in quantitative yield (33 mg). TLC: Rf~ 0.2 (10percent MeOH/DCM); 'H NMR (400 MHz, CDC13): δ 7.45-7.08 (m, 5H), 3.93 (d, J= 5.5 Hz, 1H), 3.24 (s, 3H), 3.14 (app qn, J= 6.0 Hz, 1H), 1.32 (br 2H), 1.05 (d, J= 6.5 Hz, 3H); 13C NMR (101 MHz, CDC13): δ 138.89, 128.22, 127.73, 127.60, 88.92, 57.01, 51.67, 19.19; HRMS (ESI+): Calcd. for [CioH15NO+H]+ 166.1226, Found With camphor-10-sulfonic acid, Time= 18h, T= 0 - 40 °C , Inert atmosphere
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Patent; ESS, Daniel, Halsell; FALCK, John, Russell; JAT, Jawahar, Lal; URTI, Laszlo; WO2015/103505; (2015); (A2) English View in Reaxys
H
OH
O
H 2N H 2N
H
Rx-ID: 13251690 View in Reaxys 4/18 Yield
Conditions & References Reaction Steps: 3 1.1: 96 percent / toluene / 4 h / Heating 2.1: NaH / dimethylformamide / 0.25 h / 0 °C 2.2: 87 percent / dimethylformamide / 1 h / 0 °C 3.1: 68 percent / hydrazine / aq. ethanol / 1 h / 40 °C With sodium hydride, hydrazine in ethanol, N,N-dimethyl-formamide, toluene Bertz, Steven H.; Ogle, Craig A.; Rastogi, Abhinav; Journal of the American Chemical Society; vol. 127; nb. 5; (2005); p. 1372 - 1373 View in Reaxys
O HO
O
N
H 2N
O
Rx-ID: 13261995 View in Reaxys 5/18 Yield
Conditions & References Reaction Steps: 2 1.1: NaH / dimethylformamide / 0.25 h / 0 °C 1.2: 87 percent / dimethylformamide / 1 h / 0 °C 2.1: 68 percent / hydrazine / aq. ethanol / 1 h / 40 °C With sodium hydride, hydrazine in ethanol, N,N-dimethyl-formamide Bertz, Steven H.; Ogle, Craig A.; Rastogi, Abhinav; Journal of the American Chemical Society; vol. 127; nb. 5; (2005); p. 1372 - 1373 View in Reaxys O
HN H 2N
HO
racemate
racemate
Rx-ID: 37474417 View in Reaxys 6/18 Yield
Conditions & References
99 %
With camphor-10-sulfonic acid, Time= 16h, T= 0 - 40 °C , regioselective reaction Jat, Jawahar L.; Paudyal, Mahesh P.; Gao, Hongyin; Xu, Qing-Long; Yousufuddin, Muhammed; Devarajan, Deepa; Ess, Daniel H.; Kurti, Laszlo; Falck, John R.; Science; vol. 343; nb. 6166; (2014); p. 61 - 65 View in Reaxys
H
OH
I
H 2N H
O NH 2
Rx-ID: 28240991 View in Reaxys 7/18 Yield
Conditions & References Stage 1: With potassium hydride in tetrahydrofuran, Time= 0.5h, T= 15 - 20 °C
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Stage 2: in tetrahydrofuran, Time= 1.5h, T= 20 °C Denmark, Scott E.; Ares, Jeffrey J.; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9647 - 9656 View in Reaxys O O
O
N H 2N
Rx-ID: 13249225 View in Reaxys 8/18 Yield
Conditions & References Reaction Steps: 2 1: sodium methoxide / benzene / 1 h / 0 °C 2: LiAlH4 / tetrahydrofuran / 2 h / Heating With lithium aluminium tetrahydride, sodium methylate in tetrahydrofuran, benzene Osorio-Olivares, Mauricio; Rezende, Marcos Caroli; Sepulveda-Boza, Silvia; Cassels, Bruce K.; Fierro, Angelica; Bioorganic and Medicinal Chemistry; vol. 12; nb. 15; (2004); p. 4055 - 4066 View in Reaxys Reaction Steps: 2 1: 80 percent 2: 3.6 g / H2 / Raney nickel / ethanol / 48 h / 53200 Torr / Ambient temperature With hydrogen, nickel in ethanol Ardabilchi, Nasser; Fitton, Alan O.; Hadi, A. Hamid b. A.; Thompson, J. Robin; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1710 - 1725 View in Reaxys
H
OH
O
I
H 2N
H 2N
H
Rx-ID: 39957295 View in Reaxys 9/18 Yield
Conditions & References Stage 1: With potassium hydride in tetrahydrofuran, Time= 0.166667h, T= 0 - 20 °C Stage 2: in tetrahydrofuran, Time= 1.5h Garca-Rubia, Alfonso; Laga, Eduardo; Cativiela, Carlos; Urriolabeitia, Esteban P.; Gmez-Arrays, Ramn; Carretero, Juan C.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3321 - 3331 View in Reaxys
H
OH
H 2N H
O
Me-halide
H 2N
Rx-ID: 8507519 View in Reaxys 10/18 Yield
Conditions & References With sodium hydride in tetrahydrofuran Ishii, Katsuyuki; Aoki, Shin; Koga, Kenji; Tetrahedron Letters; vol. 38; nb. 4; (1997); p. 563 - 566 View in Reaxys O
H
SASRIN-maleidobenzoic acid resin O
H 2N
Rx-ID: 13257064 View in Reaxys 11/18
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Yield
Conditions & References Reaction Steps: 3 1: butylamine; acetic acid / 1 h / Heating 2: sodium methoxide / benzene / 1 h / 0 °C 3: LiAlH4 / tetrahydrofuran / 2 h / Heating With lithium aluminium tetrahydride, sodium methylate, acetic acid, N-butylamine in tetrahydrofuran, benzene Osorio-Olivares, Mauricio; Rezende, Marcos Caroli; Sepulveda-Boza, Silvia; Cassels, Bruce K.; Fierro, Angelica; Bioorganic and Medicinal Chemistry; vol. 12; nb. 15; (2004); p. 4055 - 4066 View in Reaxys
H 2N
H
HO
H
O H 2N
I
racemate
racemate
Rx-ID: 8605451 View in Reaxys 12/18 Yield
Conditions & References With sodium hydride in tetrahydrofuran, Time= 1h, Heating, Etherification Bertrand, Michele P.; Coantic, Stephanie; Feray, Laurence; Nouguier, Robert; Perfetti, Patricia; Tetrahedron; vol. 56; nb. 24; (2000); p. 3951 - 3961 View in Reaxys O
E
H 2N racemate
Rx-ID: 37474414 View in Reaxys 13/18 Yield
Conditions & References Reaction Steps: 2 1: O-(2,4-dinitro-phenyl)-hydroxylamine; Rh2(esp)2 / 2,2,2-trifluoroethanol / 14 h / -10 °C 2: camphor-10-sulfonic acid / 16 h / 0 - 40 °C With Rh2(esp)2, camphor-10-sulfonic acid, O-(2,4-dinitro-phenyl)-hydroxylamine in 2,2,2-trifluoroethanol Jat, Jawahar L.; Paudyal, Mahesh P.; Gao, Hongyin; Xu, Qing-Long; Yousufuddin, Muhammed; Devarajan, Deepa; Ess, Daniel H.; Kurti, Laszlo; Falck, John R.; Science; vol. 343; nb. 6166; (2014); p. 61 - 65 View in Reaxys
O
E
erythro erythro NH 2
Rx-ID: 40479769 View in Reaxys 14/18 Yield
Conditions & References Reaction Steps: 2 1: [Rh2(α,α,α′,α′-tetramethyl-1,3-benzenedipropionate)2]; O-(2,4-dinitro-phenyl)-hydroxylamine / 2,2,2-trifluoroethanol / 14 h / -10 °C / |Inert atmosphere 2: camphor-10-sulfonic acid / 18 h / 0 - 40 °C / |Inert atmosphere With [Rh2(α,α,α′,α′-tetramethyl-1,3-benzenedipropionate)2], camphor-10-sulfonic acid, O-(2,4-dinitro-phenyl)-hydroxylamine in 2,2,2-trifluoroethanol Patent; ESS, Daniel, Halsell; FALCK, John, Russell; JAT, Jawahar, Lal; URTI, Laszlo; WO2015/103505; (2015); (A2) English View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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H 2N
H
HO
H
O
I H 2N
Rx-ID: 4208496 View in Reaxys 15/18 Yield
Conditions & References With sodium hydride, 1.) THF, 23 deg C, 0.5 h, 2.) THF, reflux, 1 h, Yield given. Multistep reaction Pyne, Stephen G.; Journal of Organic Chemistry; vol. 51; nb. 1; (1986); p. 81 - 87 View in Reaxys
O
H 2N
H 2N
Z
HO
O
racemate racemate
Rx-ID: 42094479 View in Reaxys 16/18 Yield
Conditions & References With [Fe(phthalocyanine)], PivO-NH2*HOTf, Time= 16h, T= 25 °C , Inert atmosphere, Overall yield = 33 percentSpectr.; regioselective reaction Legnani, Luca; Morandi, Bill; Angewandte Chemie - International Edition; vol. 55; nb. 6; (2016); p. 2248 - 2251; Angew. Chem.; vol. 128; nb. 6; (2016); p. 2288 - 2292,5 View in Reaxys
O
HO
H 2N
H 2N
E
O
racemate racemate
Rx-ID: 42094481 View in Reaxys 17/18 Yield
Conditions & References With [Fe(phthalocyanine)], PivO-NH2*HOTf, Time= 16h, T= 25 °C , Inert atmosphere, Overall yield = 56 percentSpectr.; regioselective reaction Legnani, Luca; Morandi, Bill; Angewandte Chemie - International Edition; vol. 55; nb. 6; (2016); p. 2248 - 2251; Angew. Chem.; vol. 128; nb. 6; (2016); p. 2288 - 2292,5 View in Reaxys
H
O
O
Br H
H 2N
Rx-ID: 351807 View in Reaxys 18/18 Yield
Conditions & References With ammonia, water Lewi; ; vol. 8; nb. 1; (1958); p. 31,33; ; (1960); p. 10934 View in Reaxys
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