Water → {(4S,5S)-5-[(Benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl methanesulfonate

Participants

Reaction Steps

A solution of 19.21 g of methanesulfonyl chloride (168 mmol) in methylene chloride (90 ml) was added to a solution of 35.27 g of {(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol obtained in Reference Example (1a) (140 mmol) and 29.2 ml of triethylamine (210 mmol) in methylene chloride (270 ml) under ice-cooling over 30 minutes, and the mixture was stirred at the same temperature for 20 minutes. 0.76 ml of water (42 mmol) was added to the reaction mixture, and the mixture was further stirred at room temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure and diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was washed with water, a saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 46.19 g of the crude title compound.

Provenance & Evidence