Aluminium lithium hydride → tert-butyl N-[(2R)-4-oxobutan-2-yl]carbamate
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:23])[NH:13][C@H:14]([CH3:22])[CH2:15][C:16](N(OC)C)=[O:17])([CH3:10])([CH3:9])[CH3:8]>O1CCCC1>[C:7]([O:11][C:12](=[O:23])[NH:13][C@H:14]([CH3:22])[CH2:15][CH:16]=[O:17])([CH3:10])([CH3:8])[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium aluminum hydride (5 mL, 1.0M in THF) was added slowly to a stirred solution of tert-butyl[(1R)-3-[methoxy(methyl)amino]-1-methyl-3-oxopropyl]carbamate in tetrahydrofuran (25 mL) at −40° C. under a nitrogen atmosphere. After 30 min, the reaction mixture was quenched with saturated aqueous ammonium chloride solution. The cooling bath was removed and stirring was continued for one hour. The mixture was filtered through a pad of Celite and washed with ether. The filtrate was washed sequentially with ice cold 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine, dried over magnesium sulfate, filtered and evaporated to yield the title compound as a colorless oil. MS 87.9 (M-Boc+1).