Benzyl Alcohol → HCID 68561558, compound

Participants

Reaction Steps

Add NaH (12.5 g, 60% mineral oil suspension, 312.5 mmol) in portions to a solution of benzyl alcohol (32 mL, 309.2 mmol) in N-methylpyrrolidinone (1 L). Stir the reaction mixture at r.t. until no gas evolution is detected. Add (R)-4-[(1R,2S)-3-(3,5-difluorophenyl)-1-benzyloxy-2-dibenzylaminopropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (130 g) to the mixture and warm it up to 90° C. After 45 min, allow to cool to room temperature and add saturated aqueous ammonium chloride. Dilute with ethyl acetate (2 L) and wash with saturated aqueous sodium chloride (2×1.5 L). Dry the organic layer on MgSO4, filter and concentrate. Subject residue to silical gel chromatography, eluting with 2-4% ethyl acetate in hexanes, to provide 139.45 g (94%) of the desired compound as a white solid.

Provenance & Evidence