Lithium borohydride → HCID 71020561, compound
Reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[C:28](=[O:42])[NH:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[CH:32][CH:31]=1)=O.[Li+].[BH4-]>C1COCC1>[F:41][C:38]([F:39])([F:40])[CH2:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:28]([N:6]2[CH2:7][C@@H:8]([O:10][Si:11]([C:24]([CH3:27])([CH3:25])[CH3:26])([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][C@@H:5]2[CH2:3][OH:2])=[O:42])=[CH:35][CH:34]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (2R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-[4-(2,2,2-trifluoro-ethoxy)-phenylcarbamoyl]-pyrrolidine-2-carboxylic acid methyl ester (5 g, 8.33 mmol) in THF (30 mL) was added LiBH4 (2M in THF, 6.25 mL) at 0° C. and stirred for 2 h. The mixture was quenched with AcOH at 0° C. and diluted with DCM. The organic layer was washed with sat NaHCO3 solution, dried over Na2SO4 and concentrated. The residue was purified through column chromatography over silica (elution with 40% ethyl acetate in hexane) to yield 4.3 g (91%) of the title compound as pale yellow sticky liquid. LC-MS: 573.6 [M+1]+.