Water → HCID 86674673, compound

Participants

Reaction Steps

Under a Nitrogen atmosphere was mixed NAH (91.5 g) in DMF (2 L) and (R)-isopropyl 1-(3-(benzyloxy)-2-hydroxypropyl)cyclopropane-1-sulfonate (715 g) in DMF (1 L) at a temperature between −5° C. and 5° C. for 140 minutes. After stirring for a further 5 minutes, NaI (5.1 g) was added. After BnCl (289.5 g) in DMF (300 mL) was added gradually, the reaction mixture was warmed slowly to room temperature and stirred for approximately 16 hours until HPLC analysis showed the reaction was complete. The reaction mixture was cooled to −5° C. and water (4 L) was added followed by MTBE (2 L (×2)) with stirring for 20 minutes. The organic layer was separated, washed with water (2 L (×2)), brine (2 L), dried over Na2SO4 and concentrated to give 830 g of product.

Provenance & Evidence