Sodium borohydride → (2R,3S,5R)-5-[2-Amino-3-(3-benzyloxy-5-fluoro-phenyl)-1-hydroxy-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Add sodium borohydride (1.66 g, 43.87 mmol) to (2R,3S,5R)-5-[(1R,2S)-3-(3-benzyloxy-5-fluoro-phenyl)-1-hydroxy-2-nitro-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (5.89 g, 9.97 mmol) and nickel chloride (2.07 g, 15.95 mmol) in methanol (100 mL) at room temperature and stir 30 minutes. Add water (˜10 mL) and concentrate. Dilute with ethyl acetate and filter through celite. Partition between ethyl acetate and saturated aqueous sodium chloride. Wash the organic layer with saturated aqueous sodium chloride, dry (sodium sulfate), filter and concentrate to give 4.32 g (77.3%) of the desired compound as a white solid.

Provenance & Evidence