(2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-methoxypyridin-4-yl)propanoic acid → tert-butyl {(1S)-2-hydroxy-1-[(2-methoxypyridin-4-yl)methyl]ethyl}carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[OH:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH3:21])[CH:15]=1Participants
3
Procedure
To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-methoxypyridin-4-yl)propanoic acid (1.3 g, 4.4 mmol) in tetrahydrofuran (5.0 mL) with stirring, 1.0 M borane-THF complex in THF (13 mL) was added dropwise to keep the internal temperature at 0° C. (about 15 min). After addition, the mixture was stirred at rt for 3 h, cooled with an ice-bath, quenched with AcOH:MeOH (1:5, 5 mL), partitioned between saturated aqueous NaHCO3 and DCM, dried over Na2SO4, filtered, and evaporated under reduced pressure to give 0.5 g (40% yield) of the desired product. LC-MS found: 283.0 (M+H)+.