Diisobutylaluminumhydride → (3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-3-methylmorpholin-2-ol

Participants

Reaction Steps

Add diisobutylaluminum hydride (2.48 mL, 2.48 mmol, 1.0 M in toluene) to a solution of (3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-3-methylmorpholin-2-one (1.09 g, 1.91 mmol) in dry toluene (20 mL) at −78° C. under nitrogen and stir at this temperature for 15 minutes. Quench by adding methanol (1.0 mL). Add saturated aqueous potassium sodium tartrate (Rochelle salt) and ethyl acetate, warm to room temperature and stir vigorously for 30 minutes. Separate the organic layer and extract the aqueous with ethyl acetate. Combine the organic layers, dry (magnesium sulfate), filter and concentrate to give the desired compound as a mixture of the two possible epimers as a white solid which is used directly in the next step without further purification (1.08 g, 99% yield).

Provenance & Evidence