Potassium;tri(butan-2-yl)boranuide → tert-Butyl {(3S)-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methyl-1-[(2S,4S)-5-oxo-4-(propan-2-yl)oxolan-2-yl]pentyl}carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 5.51 g of (2S,5S,7S)-5-tert-butoxycarbonylamino-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid in 25 mL of tetrahydrofuran is cooled to −30° C. and 10 mL of a 1.0 M solution of K-selectride in tetrahydrofuran is added dropwise within 30 minutes. The mixture is stirred for 2 hours at 30° C. and warmed to 0° C. and stirred for 16 hours. The reaction mixture is quenched with 50 mL of 1.0 M hydrochloric acid and extracted three times with 100 mL of dichloromethane. The organic layer is dried and the solvent is removed to give the title compound as a semi solid.

Provenance & Evidence