Methanol → Ethyl 4-(4-amino-3-phenylbutanamido)benzoate
Reaction equation
[N+:1]([CH2:4][CH:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:6][C:7]([NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1)=[O:8])([O-])=O.CO>>[NH2:1][CH2:4][CH:5]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:6][C:7]([NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1)=[O:8]Participants
Procedure
Ref. J. Org. Chem., 2000, 65, 8001. To a stirred solution of nitro compound 47 (0.749 g, 2.10 mmol) and NiCl2.6H2O (1.99 g, 8.40 mmol) in methanol (10 ml) NaBH4 (0.719 g, 18.93 mmol) was added portionwise over 20 min at 0° C. After stirring for 15 at room temperature, the solvent was removed under reduced pressure. Water (20 ml) and ethyl acetate (40 ml) were added to the solid residue. The resulting mixture was filtered through a celite bed which was washed with ethyl acetate (20 ml). After collecting the filtrate, the organic phase was separated, dried over Na2SO4 and the solvent removed under reduced pressure to afford amine 51 as an off white solid (0.596 g, 1.83 mmol, 87%). The amine was used in the next step without further purification.
Workup
- customthe solvent was removed under reduced pressure
- additionWater (20 ml) and ethyl acetate (40 ml) were added to the solid residue
- filtrationThe resulting mixture was filtered through a celite bed which
- washwas washed with ethyl acetate (20 ml)
- customAfter collecting the filtrate
- customthe organic phase was separated
- dry with materialdried over Na2SO4
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-8545c269d1274ba1afb037607ca971e0
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07960434B2
Reaction notes
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