5. N–2 x G'zvezdochka', 2 keto [Reaxys, Reactions (49); 2016-03-23] by Asch

Query Query G* N

Date

49 reactions in Reaxys

2016-03-23 08h:21m:58s (EST)

1. Query

Results G*

Search as: As drawn, No salts, No mixtures

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Rx-ID: 628093 View in Reaxys 1/49 Yield

Conditions & References N,N-Dimethyl-2-(1-octyl-1H-indol-3-yl)ethanamine (N1-octyl-N10,N10-dimethyltryptamine, 6d): General procedure: To a suspension of LiAlH4 (2.00 g, 52.6 mmol) in dry THF (200 mL) at 0 °C, was added dropwise

79 %

a solution of N,N-dimethyl-2-(1-octyl-1H-indol-3-yl)-2-oxoacetamide (10a, 2.00 g, 6.07 mmol) in dry THF. The mixture was refluxed with stirring for 4 h and was cooled to rt and then with an ice-water bath. Aqueous THF (1:1) was added carefully, the solid was removed by filtration and the solvents were evaporated under reduced pressure. Chromatography (DCM:MeOH 9:1) afforded 1.17 g (64 percent) of the desired product as a clear oil. With lithium aluminium tetrahydride in tetrahydrofuran, T= 0 °C , Reflux Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727 View in Reaxys With lithium aluminium tetrahydride Barlow; Khan; British Journal of Pharmacology and Chemotherapy; vol. 14; (1959); p. 99,101 View in Reaxys

O O HN

Rx-ID: 2303657 View in Reaxys 2/49 Yield 97 %

Conditions & References With lithium aluminium tetrahydride, sulfuric acid in tetrahydrofuran, Time= 1.25h, Ambient temperature Pelcman; Gribble; Tetrahedron Letters; vol. 31; nb. 17; (1990); p. 2381 - 2384 View in Reaxys

97 %

With aluminium hydride in tetrahydrofuran, Time= 1.25h, Ambient temperature Gribble; Pelcman; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3636 - 3642 View in Reaxys

91 %

With lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, Inert atmosphere, Reflux Aubry, Carine; Wilson, A. James; Emmerson, Daniel; Murphy, Emma; Chan, Yu Yam; Dickens, Michael P.; Garcia, Marcos D.; Jenkins, Paul R.; Mahale, Sachin; Chaudhuri, Bhabatosh; Bioorganic and Medicinal Chemistry; vol. 17; nb. 16; (2009); p. 6073 - 6084 View in Reaxys With lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, Time= 6h, Heating Aubry, Carine; Patel, Asma; Mahale, Sachin; Chaudhuri, Bhabatosh; Marechal, Jean-Didier; Sutcliffe, Michael J.; Jenkins, Paul R.; Tetrahedron Letters; vol. 46; nb. 9; (2005); p. 1423 - 1425 View in Reaxys

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Rx-ID: 25346888 View in Reaxys 3/49 Yield

Conditions & References 2.d : EXAMPLE 2 d. A solution of 8.7 g of 1-(indol-3-ylglyoxyloyl)-4-(o-tolyloxy)piperidine in 80 ml. of tetrahydrofuran is added dropwise to a stirred suspension of 4.2 g of lithium aluminum hydride in 120 ml. of tetrahydrofuran. After addition is complete, the mixture is stirred and refluxed for 3 hours under nitrogen. The reaction mixture is then cooled and excess hydride is carefully destroyed with water. The mixture is filtered, the filter cake washed with tetrahydrofuran, and the tetrahydrofuran is removed under reduced pressure to give an oil. The oil is evacuated at about 3 mm. overnight, and then rubbed with a glass rod in the presence of hexane to give a white solid. the solid is recrystallized from a benzene and hexane mixture (charcoal treatment) to give off-white crystals. These crystals are recrystallized from an isopropanol and water mixture to give white flakes of 3-{2-[4-(o-tolyloxy)piperidyl]ethyl}indole, m.p. 88°-90° C. Analysis: Calculated for C22 H26 N2 O: 79.00percent C; 7.83percent H; 8.37percent N. Found: 78.97percent C; 7.82percent H; 8.26percent N. With hexane in tetrahydrofuran Patent; American Hoechst Corporation; US4031221; (1977); (A1) English View in Reaxys

N O

Rx-ID: 9830859 View in Reaxys 4/49 Yield 99 %

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, Inert atmosphere, Reflux Aubry, Carine; Wilson, A. James; Emmerson, Daniel; Murphy, Emma; Chan, Yu Yam; Dickens, Michael P.; Garcia, Marcos D.; Jenkins, Paul R.; Mahale, Sachin; Chaudhuri, Bhabatosh; Bioorganic and Medicinal Chemistry; vol. 17; nb. 16; (2009); p. 6073 - 6084 View in Reaxys With lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, Time= 6h, Heating Aubry, Carine; Patel, Asma; Mahale, Sachin; Chaudhuri, Bhabatosh; Marechal, Jean-Didier; Sutcliffe, Michael J.; Jenkins, Paul R.; Tetrahedron Letters; vol. 46; nb. 9; (2005); p. 1423 - 1425 View in Reaxys

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O O HN

Rx-ID: 2163193 View in Reaxys 5/49 Yield

Conditions & References

60 %

With sodium (trifluoroacetoxy)borohydride in tetrahydrofuran, Time= 20h, Heating Pelcman; Gribble; Tetrahedron Letters; vol. 31; nb. 17; (1990); p. 2381 - 2384 View in Reaxys

60 %

With sodium tetrahydroborate, trifluoroacetic acid in tetrahydrofuran, Time= 20h, ice bath cooling up to reflux Gribble; Pelcman; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3636 - 3642 View in Reaxys

O HN

Rx-ID: 9831362 View in Reaxys 6/49 Yield

Conditions & References

78 %

N O

Rx-ID: 2818381 View in Reaxys 7/49 Yield 35 %

Conditions & References With lithium aluminium tetrahydride in ethylene glycol dimethyl ether, Time= 18h, Heating Agarwal, Jagdish C.; Sharma, M.; Saxena, A. K.; Kishor, K.; Bhargava, K. P.; Shanker, K.; Journal of the Indian Chemical Society; vol. 57; nb. 7; (1980); p. 742 - 743 View in Reaxys 17 : 3-[2-(4-hydroxy-4-phenylpiperidinyl)ethyl]indole EXAMPLE 17 3-[2-(4-hydroxy-4-phenylpiperidinyl)ethyl]indole

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A solution of 17.0 g. (0.049 mole) of 1-(indol-3-ylglyoxyloyl)-4-phenyl-4-piperidinol in 100 ml. of tetrahydrofuran was reduced in the usual way with 7.4 g. (0.195 mole) of lithium aluminum hydride in 200 ml. of tetrahydrofuran. After the usual workup 11.6 g. of oil was obtained which was crystallized from benzene-isooctane yielding 8.6 g. (55percent) of product which melted at 133°-137° C. Another recrystallization from benzene raised the melting point to 137°-139° C. The analytical sample melted at 137°-139° C. Analysis.--Calculated for C21 H24 N2 O (percent): C, 78.71; H, 7.55; N, 8.74. Found (percent): C, 78.30; H, 7.36; N, 8.60. in tetrahydrofuran Patent; A. H. Robins Company, Incorporated; US28973; (1976); (E1) English View in Reaxys

N 2

Rx-ID: 11192118 View in Reaxys 8/49 Yield

Conditions & References

89 %

With lithium aluminium deuteride in tetrahydrofuran Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368 View in Reaxys

80 %

With lithium aluminium deuteride in tetrahydrofuran, Inert atmosphere, Microwave irradiation Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429 View in Reaxys

N O

Rx-ID: 9831656 View in Reaxys 9/49 Yield 57 %

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O O

ethereal hydrogen chloride

O Cl

solvated ether

N H

Rx-ID: 25269332 View in Reaxys 10/49 Yield

Conditions & References 8 : 3-{2-[3-(o-methoxyphenoxy)pyrrolidinyl]ethyl} indole hydrochloride EXAMPLE 8 3-{2-[3-(o-methoxyphenoxy)pyrrolidinyl]ethyl} indole hydrochloride A solution of 13.5 g. (0.037 mole) of 1 -(indole-3-ylglyoxyloyl)-3-(o-methoxyphenoxy)pyrrolidine in 50 ml. of anhydrous tetrahydrofuran was added dropwise to a stirred slurry of 7 g. (0.18 mole) of lithium aluminum hydride in 150 ml. of anhydrous tetrahydrofuran. The reaction mixture was worked up in the usual manner and the oily basic material which was isolated was dissolved in ether and treated with ethereal hydrogen chloride. The isolated hydrochloride weighed 10.7 g. (73percent) and melted with decomposition (gas evolution) near a55° C. as a result of solvated ether. Thin layer chromatography of a sample of regenerated free base showed a single spot. Analysis.--Calculated for C21 H25 ClN2 O2 (percent): C, 67.64; H, 6.76; N, 7.51. Found (after drying at 120°) (percent): C, 67.72; H, 7.07; N, 7.43. in tetrahydrofuran Patent; A. H. Robins Company, Incorporated; US28973; (1976); (E1) English View in Reaxys

O N

NH 2 N

N N

N H

Rx-ID: 25281979 View in Reaxys 11/49 Yield

Conditions & References 1.b : 3-[2-(4-Aminopiperazin-1-yl)ethyl]indole b. To a stirred mixture of 9.0 g of lithium aluminum hydride in 400 ml. of 1,2-dimethoxyethane is added 10.52 g (0.037 mol) of 1-(indol-3-ylglyoxyloyl)-4-nitrosopiperazine slowly to maintain reaction temperature below 35° C. After all the material is added, the mixture is refluxed for 14-16 hours. The reaction mixture is cooled to -5° C. and a solution of 50 ml. of water and 50 ml. of 1,2-dimethoxyethane is slowly added while maintaining the temperature below 15° C. Another 50 ml. of water is added, and the mixture is then filtered. The solvent is removed from the filtrate and the residual solid is recrystallized from benzene, producing the pure crystals of 3-[2-(4-aminopiperazin-1-yl)ethyl]indole, m.p. 115°-117° C. Analysis:

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Calculated for C14 H20 N4:68.82percent C; 8.25percent H; 22.93percent N Found:68.70percent C; 8.17percent H; 22.55percent N. in ethylene glycol dimethyl ether, water Patent; American Hoechst Corporation; US3997539; (1976); (A1) English View in Reaxys

OH H

N O

Rx-ID: 25282041 View in Reaxys 12/49 Yield

Conditions & References 19 : 3-[2-(4-hydroxy-4-m-trifluoromethylphenylpiperidinyl)ethyl] indole hydrochloride EXAMPLE 19 3-[2-(4-hydroxy-4-m-trifluoromethylphenylpiperidinyl)ethyl] indole hydrochloride A solution of 37 g. (0.089 mole (of 1-(indol-3-yl glyoxyloyl)-4-(m-trifluoromethylphenyl)-4-piperidinol in 100 ml. of tetrahydrofuran was added dropwise under nitrogen to a stirred suspension of 16.9 g. (0.445 mole) of lithium aluminum hydride in 100 ml. of tetrahydrofuran. The reaction was refluxed two hours and then worked up in the usual manner. Recrystallization of the isolated solid from benzene-isooctane gave 26.5 g. (70percent) of pure product which was shown by nuclear magnetic resonance to be a benzene solvate. in tetrahydrofuran Patent; A. H. Robins Company, Incorporated; US28973; (1976); (E1) English View in Reaxys

N H

Rx-ID: 25346889 View in Reaxys 13/49 Yield

Conditions & References 3.d : EXAMPLE 3 d. A solution of 10.0 of 1-(indol-3ylglyoxyloyl)-4-(m-tolyloxy)piperidine in 205 ml. of tetrahydrofuran is added dropwise to a stirred suspension of 4.8 g of lithium aluminum hydride in 140 ml. of tetrahydrofuran. After the addition is complete, the mixture is stirred and refluxed for 3 hours under nitrogen, cooled, and the excess hydride is carefully destroyed with water. The inorganic precipitate is filtered off and washed with tetrahydrofuran. The filtrate is concentrated, under reduced pressure, to a clear oil which crystallizes to a white solid. The solid is recrystallized from acetonitrile to give white needles of 3-{2-[4-(m-tolyloxy)piperidyl]ethyl}indole, m.p. 145°-146° C. Analysis:

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Calculated for C22 H26 N2 O: 79.00percent C; 7.83percent H; 8.37percent N. Found: 78.92percent C; 8.01percent H; 8.34percent N. in tetrahydrofuran Patent; American Hoechst Corporation; US4031221; (1977); (A1) English View in Reaxys

O O

N H

Rx-ID: 25346890 View in Reaxys 14/49 Yield

Conditions & References 4.c : EXAMPLE 4 c. A suspension of 4.0 g of 1-(indol-3-ylglyoxyloyl)-4-(p-tolyloxy)piperidine in 40 ml. of tetrahydrofuran is added dropwise to a stirred suspension of 2.1 g of lithium aluminum hydride in 60 ml. of tetrahydrofuran. After addition is complete the mixture is stirred and refluxed for 3 hours under nitrogen. After cooling, the excess hydride is carefully destroyed with water. The mixture is filtered, the filter cake is washed with tetrahydrofuran, and the filtrate is concentrated to a colorless oil under reduced pressure. The oil is kept under vacuum for 24 hours and then permitted to stand for several days. The oil slowly solidifies to a white solid. The solid is collected, washed with petroleum ether (b.p. 30°-60°) and recrystallized from an ethanol and water mixture to give white needles of 3-{2-[4-(p-tolyloxy)piperidyl]ethyl}indole, m.p. 115°-117° C. Analysis Calculated for C22 H26 N2 O: 79.00percent C; 7.84percent H; 8.38percent N. Found: 79.10percent C; 7.89percent H/ 8.35percent N. in tetrahydrofuran Patent; American Hoechst Corporation; US4031221; (1977); (A1) English View in Reaxys

O O

N H

Rx-ID: 25346891 View in Reaxys 15/49 Yield

Conditions & References 9.d : EXAMPLE 9 d. By following the manipulative procedure described in Example 2(d), 2.6 g of lithium aluminum hydride in 80 ml. of tetrahydrofuran and 6.0 g of 1-(indol-3-ylglyoxyloyl)-4-(p-fluorophenoxy)piperidine in 60 ml. of tetrahydrofuran are allowed to react to produce a white solid. The solid is recrystallized from isopropanol, and then from an ethanol and water mixture to give colorless cubes of 3{2-[4-(p-fluorophenoxy)piperidyl]ethyl}indole, m.p. 109°-111° C. Analysis:

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Calculated for C21 H23 N2 FO: 74.53percent C; 6.85percent H; 8.28percent N. Found: 74.68percent C; 6.79percent H; 8.28percent N. in tetrahydrofuran, ethanol, water Patent; American Hoechst Corporation; US4031221; (1977); (A1) English View in Reaxys F

N O

Rx-ID: 25346897 View in Reaxys 16/49 Yield

Conditions & References 15.e : EXAMPLE 15 e. By following the manipulative procedure described in Example 2(d), 0.7 g of lithium aluminum hydride in 30 ml. of tetrahydrofuran and 1.5 g of 1-(indol-3-ylglyoxyloyl)-3-(p-fluorophenoxy)azetidine in 30 ml. of tetrahydrofuran are reacted to produce a white solid. The solid is recrystallized twice from an ethanol and water mixture to give colorless needles of 3-{2-[3-(p-fluorophenoxy)azetidinyl]ethyl}indole, m.p. 111°-113°. Analysis: Calculated for C19 H19 FN2 O: 73.35percent C; 6.15percent H; 9.00percent N; 6.10percent F. Found: 73.38percent C; 6.34percent H; 9.01percent N; 5.92percent F. in tetrahydrofuran Patent; American Hoechst Corporation; US4031221; (1977); (A1) English View in Reaxys

N O

N H

Rx-ID: 254956 View in Reaxys 17/49 Yield 70 %

Conditions & References With lithium aluminium tetrahydride Somei, Masanori; Kobayashi, Kensuke; Tanii, Keiko; Mochizuki, Toshihiko; Kawada, Yumiko; Fukui, Yoshikazu; Heterocycles; vol. 40; nb. 1; (1995); p. 119 - 122 View in Reaxys With lithium aluminium tetrahydride Kondo et al.; ; Labor Nr. 10 <1959> 1, 8; engl. Ausg. S. 33, 42 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, benzene, Time= 2h, Heating, Reduction Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414 View in Reaxys With lithium aluminium tetrahydride in 1,4-dioxane, Reflux

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Chu, Uyen B.; Vorperian, Sevahn K.; Satyshur, Kenneth; Eickstaedt, Kelsey; Cozzi, Nicholas V.; Mavlyutov, Timur; Hajipour, Abdol R.; Ruoho, Arnold E.; Biochemistry; vol. 53; nb. 18; (2014); p. 2956 - 2965 View in Reaxys

O O

H B

N H

Rx-ID: 25339785 View in Reaxys 18/49 Yield

Conditions & References 5.d : EXAMPLE 5 d. 60 ml. of a 1M solution of boron trihydride in tetrahydrofuran are added dropwise to a stirred solution of 7.0 g of 1(indol-3-ylglyoxyloyl)-4-(p-chlorophenoxy)piperidine in 135 ml. of tetrahydrofuran under nitrogen. The solution is stirred at ambient temperature for 18 hours and the tetrahydrofuran is removed under reduced pressure to give a white boron complex. The complex is destroyed by refluxing in 135 ml. of methanol with a few drops of glacial acetic acid. After cooling, the methanol is removed under reduced pressure to give a yellow oil. The oil is dissolved in ether, the ether is washed with water, dried and removed under reduced pressure to give a yellow oil. After standing under vacuum for a week, the oil crystallizes to a yellow solid. The solid is recrystallized from toluene and then from an ethanol and water mixture to give white crystals of 3-{2-[4-(pchlorophenoxy)piperidyl]ethyl}indole, m.p. 132°-133° C. Analysis: Calculated for C21 H23 ClN2 O: 71.07percent C; 6.53percent H, 7.90percent N; 9.99percent Cl. Found: 70.87percent C; 6.71percent H; 7.80percent N; 10.01percent Cl. in tetrahydrofuran, methanol, ethanol, water Patent; American Hoechst Corporation; US4031221; (1977); (A1) English View in Reaxys

H B H

H N

N H

Rx-ID: 25339786 View in Reaxys 19/49 Yield

Conditions & References 6.b : EXAMPLE 6 b. 49 ml. of a 1M solution of boron trihydride in tetrahydrofuran are added dropwise to a stirred suspension of 5.3 g of 1(indol-3-ylglyoxyloyl)-4-(m-chlorophenoxy)piperidine in 100 ml. of tetrahydrofuran under nitrogen. After an initial evolution of gas, the solution turns yellow and is stirred at ambient temperature for 13 hours. The tetrahydrofuran is removed under reduced pressure to give a solid white borane complex. The complex is destroyed by refluxing in 100 ml. of methanol with several drops of glacial acetic acid for one hour. After cooling, the methanol is removed under reduced pressure, leaving a yellow oil. The oil is evacuated at about 3 mm. for 72 hours and a gummy solid forms.

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The solid is recrystallized from acetonitrile and then from an ethanol and water mixture to give white microcrystals of 3{2-[4-(m-chlorophenoxy)piperidyl]ethyl}indole, m.p. 120°-123° C. Analysis: Calculated for C21 H23 ClN2 O: 71.07percent C; 6.53percent H; 7.90percent N; 9.99percent Cl. Found: 71.20percent C; 6.57percent H; 7.88percent N; 10.11percent Cl. in tetrahydrofuran, methanol, ethanol, water Patent; American Hoechst Corporation; US4031221; (1977); (A1) English View in Reaxys

Rx-ID: 25349045 View in Reaxys 20/49 Yield

Conditions & References 32 : EXAMPLE 32 EXAMPLE 32 A stirred suspension under nitrogen of 1.5 g of lithium aluminum hydride in 150 ml of tetrahydrofuran is treated with a solution of 2,3-dihydro-1'-(indol-3-ylglyoxyloyl)spiro[benzofuran-2,4'-piperidine], Example 22, in 75 ml of tetrahydrofuran according to the procedure of Example 22 to provide a tan solid. The solid is successively recrystallized from an ethyl alcohol-water mixture, chromatographed through a silica gel column with a 2percent methyl alcohol in chloroform eluant and recrystallized from ethyl alcohol to provide the product, 2,3-dihydro-1'-[2-(3-indolyl)ethyl]spiro[benzofuran-2,4'-piperidine], mp 167°-169° C. Analysis: Calculated for C22 H24 N2 O: 79.48percentC; 7.28percentH; 8.43percentN. Found: 79.38percentC; 7.34percentH; 8.45percentN. in tetrahydrofuran, chloroform Patent; American Hoechst Corporation; US4166119; (1979); (A1) English View in Reaxys

N 2H

N H

Rx-ID: 28198064 View in Reaxys 21/49 Yield 78 %

Conditions & References With lithium aluminium deuteride in tetrahydrofuran, Inert atmosphere, Microwave irradiation Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429 View in Reaxys

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N 2H

N H

Rx-ID: 28198065 View in Reaxys 22/49 Yield

Conditions & References

76 %

N 2

N H

Rx-ID: 28198066 View in Reaxys 23/49 Yield

Conditions & References

78 %

2 2H

O NH

N 2H

Rx-ID: 28198067 View in Reaxys 24/49 Yield

Conditions & References

80 %

O NH

N 2H

Rx-ID: 28198068 View in Reaxys 25/49 Yield 76 %

Conditions & References With lithium aluminium deuteride in tetrahydrofuran, Inert atmosphere, Microwave irradiation

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Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429 View in Reaxys

N 2H

N H

Rx-ID: 28198072 View in Reaxys 26/49 Yield

Conditions & References

78 %

N 2H

N H

Rx-ID: 28198077 View in Reaxys 27/49 Yield

Conditions & References

78 %

Rx-ID: 2988698 View in Reaxys 28/49 Yield

Conditions & References

72 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 6h, Heating Afsah, El-Sayed M.; Jackson, Anthony H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); nb. 8; (1984); p. 1929 - 1932 View in Reaxys

O O HN

Rx-ID: 13299107 View in Reaxys 29/49

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Yield

Conditions & References Reaction Steps: 2 1: LiAlH4 / tetrahydrofuran; diethyl ether / 6 h / Heating 2: 55 percent / MnO2 / CHCl3 / 60 h / Heating With manganese(IV) oxide, lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, chloroform Aubry, Carine; Patel, Asma; Mahale, Sachin; Chaudhuri, Bhabatosh; Marechal, Jean-Didier; Sutcliffe, Michael J.; Jenkins, Paul R.; Tetrahedron Letters; vol. 46; nb. 9; (2005); p. 1423 - 1425 View in Reaxys Reaction Steps: 2 1: 97 percent / AlH3 / tetrahydrofuran / 1.25 h / Ambient temperature 2: 99 percent / MnO2 / CHCl3 / 4 h / Heating With aluminium hydride, manganese(IV) oxide in tetrahydrofuran, chloroform Gribble; Pelcman; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3636 - 3642 View in Reaxys Reaction Steps: 2 1: 97 percent / LiAlH4, H2SO4 / tetrahydrofuran / 1.25 h / Ambient temperature 2: 99 percent / MnO2 / CHCl3 / 4 h / Heating With manganese(IV) oxide, lithium aluminium tetrahydride, sulfuric acid in tetrahydrofuran, chloroform Pelcman; Gribble; Tetrahedron Letters; vol. 31; nb. 17; (1990); p. 2381 - 2384 View in Reaxys

N H

Rx-ID: 28198062 View in Reaxys 30/49 Yield

Conditions & References

74 %

N 2H

N H

Rx-ID: 28198063 View in Reaxys 31/49 Yield 74 %

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N 2H

O NH

Rx-ID: 28198069 View in Reaxys 32/49 Yield

Conditions & References

70 %

N H HN

Rx-ID: 3007415 View in Reaxys 33/49 Yield

Conditions & References

64 %

H N

HN N

N O

N H

Rx-ID: 3010135 View in Reaxys 34/49 Yield

Conditions & References

61 %

O O HN

Rx-ID: 20214584 View in Reaxys 35/49

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Yield

Conditions & References Reaction Steps: 2 1: 60 percent / NaBH4, CF3COOH / tetrahydrofuran / 20 h / ice bath cooling up to reflux 2: 90 percent / POCl3 / dimethylformamide / 3 h / Ambient temperature With sodium tetrahydroborate, trifluoroacetic acid, trichlorophosphate in tetrahydrofuran, N,N-dimethyl-formamide Gribble; Pelcman; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3636 - 3642 View in Reaxys Reaction Steps: 2 1: 60 percent / NaBH3OCOCF3 / tetrahydrofuran / 20 h / Heating 2: 90 percent / POCl3 / 3 h / Ambient temperature With sodium (trifluoroacetoxy)borohydride, trichlorophosphate in tetrahydrofuran Pelcman; Gribble; Tetrahedron Letters; vol. 31; nb. 17; (1990); p. 2381 - 2384 View in Reaxys

O O HN

Rx-ID: 20216989 View in Reaxys 36/49 Yield

Conditions & References Reaction Steps: 3 1: 97 percent / AlH3 / tetrahydrofuran / 1.25 h / Ambient temperature 2: 99 percent / MnO2 / CHCl3 / 4 h / Heating 3: 90 percent / POCl3 / dimethylformamide / 3 h / Ambient temperature With aluminium hydride, manganese(IV) oxide, trichlorophosphate in tetrahydrofuran, chloroform, N,N-dimethyl-formamide Gribble; Pelcman; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3636 - 3642 View in Reaxys Reaction Steps: 3 1: 97 percent / LiAlH4, H2SO4 / tetrahydrofuran / 1.25 h / Ambient temperature 2: 99 percent / MnO2 / CHCl3 / 4 h / Heating 3: 90 percent / POCl3 / 3 h / Ambient temperature With manganese(IV) oxide, lithium aluminium tetrahydride, sulfuric acid, trichlorophosphate in tetrahydrofuran, chloroform Pelcman; Gribble; Tetrahedron Letters; vol. 31; nb. 17; (1990); p. 2381 - 2384 View in Reaxys

N O

Rx-ID: 410527 View in Reaxys 37/49 Yield

Conditions & References With lithium aluminium tetrahydride Huffman; Journal of the American Chemical Society; vol. 80; (1958); p. 5193

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View in Reaxys

Rx-ID: 3612775 View in Reaxys 38/49 Yield

Conditions & References

40 %

With lithium aluminium tetrahydride in ethylene glycol dimethyl ether, Time= 18h, Heating Agarwal, Jagdish C.; Sharma, M.; Saxena, A. K.; Kishor, K.; Bhargava, K. P.; Shanker, K.; Journal of the Indian Chemical Society; vol. 57; nb. 7; (1980); p. 742 - 743 View in Reaxys

OH N

N O

Rx-ID: 3613488 View in Reaxys 39/49 Yield

Conditions & References

35 %

Rx-ID: 3612774 View in Reaxys 40/49 Yield

Conditions & References

30 %

Rx-ID: 2845454 View in Reaxys 41/49 Yield

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 7h, Heating, Yield given Ashcroft, William R.; Martinez, Silvio J.; Joule, John, A.; Tetrahedron; vol. 37; nb. 17; (1981); p. 3005 - 3007 View in Reaxys

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N O

Rx-ID: 13323202 View in Reaxys 42/49 Yield

Conditions & References Reaction Steps: 2 1: LiAlH4 / tetrahydrofuran; diethyl ether / 6 h / Heating 2: MnO2 / CHCl3 / 60 h / Heating With manganese(IV) oxide, lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, chloroform Aubry, Carine; Patel, Asma; Mahale, Sachin; Chaudhuri, Bhabatosh; Marechal, Jean-Didier; Sutcliffe, Michael J.; Jenkins, Paul R.; Tetrahedron Letters; vol. 46; nb. 9; (2005); p. 1423 - 1425 View in Reaxys

O HN

Rx-ID: 13323495 View in Reaxys 43/49 Yield

O HN

Rx-ID: 13323704 View in Reaxys 44/49 Yield

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Rx-ID: 20689416 View in Reaxys 45/49 Yield

Conditions & References Reaction Steps: 2 1: LiAlH4 / tetrahydrofuran / 7 h / Heating 2: 1.) t.BuOK, 2.) aqueous AcOH (50percent) / 1.) DMSO, 90-110 deg C, 2 weeks, 2.) 95 deg C, 4 h With lithium aluminium tetrahydride, potassium tert-butylate, acetic acid in tetrahydrofuran Ashcroft, William R.; Martinez, Silvio J.; Joule, John, A.; Tetrahedron; vol. 37; nb. 17; (1981); p. 3005 - 3007 View in Reaxys

N O

Rx-ID: 463701 View in Reaxys 46/49 Yield

Conditions & References With lithium aluminium tetrahydride Nogradi; Monatshefte fuer Chemie; vol. 88; (1957); p. 768,776 View in Reaxys Patent; Upjohn Co.; US2870162; (1954) View in Reaxys

N O

Rx-ID: 294052 View in Reaxys 47/49 Yield

Conditions & References With lithium aluminium tetrahydride Nogradi; Monatshefte fuer Chemie; vol. 88; (1957); p. 768,776 View in Reaxys

N O

Rx-ID: 340523 View in Reaxys 48/49 Yield

Conditions & References With lithium aluminium tetrahydride Nogradi; Monatshefte fuer Chemie; vol. 88; (1957); p. 768,776 View in Reaxys

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Rx-ID: 356898 View in Reaxys 49/49 Yield

Conditions & References With tetrahydrofuran, lithium aluminium tetrahydride Nogradi; Monatshefte fuer Chemie; vol. 88; (1957); p. 768,776 View in Reaxys

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