Sodium Iodide → (4S,5S)-4-[(Benzyloxy)methyl]-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane

Participants

Reaction Conditions

Reaction Steps

A solution of 46.19 g of the crude {(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl methanesulfonate obtained in Reference Example (1b) (140 mmol) and 62.87 g of sodium iodide (419 mmol) in acetonitrile (420 ml) was stirred at 80° C. for 22 hours. The reaction mixture was cooled and then concentrated under reduced pressure and diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was washed with a 1.5 M sodium sulfite aqueous solution, water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 49.20 g of the crude title compound.

Provenance & Evidence