Sodium borohydride → HCID 117966926, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]([C@H:16]2[CH2:21][C:20](=[O:22])[CH2:19][CH2:18][N:17]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:15])[CH3:12])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>CO.O>[OH:22][CH:20]1[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:16]([C:14](=[O:15])[NH:13][C@H:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[CH3:12])[CH2:21]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To an ice cooled solution of (R)-tert-butyl 2-(((S)-1-(4-(methoxycarbonyl)phenyl)ethyl)carbamoyl)-4-oxopiperidine-1-carboxylate (D60) (300 mg, 0.75 mmol) in MeOH (25 ml) under nitrogen, NaBH4 (142 mg, 3.75 mmol) was added portionwise and the resulting mixture was stirred at RT for 18 hrs. The mixture was diluted with water (10 ml) and extracted with EtOAc (3×10 ml). The organic phases were collected, washed with NaCl sat. (20 ml) dried over Na2SO4 and evaporated in vacuo to afford the title compound (D61) (261 mg).