Methyl chloroformate → HCID 123665052, compound

Participants

Reaction Steps

To a solution of 403 mg of (S)—N-[(2R)-2-(3-bromophenyl)-1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-yl]-2-methylpropane-2-sulfinamide in 4 ml of THF was added 1.4 ml of a 1.63 M n-butyllithium/hexane solution at −78° C., followed by stirring for 30 minutes, and then 283 μl of methyl chloroformate was added dropwise thereto, followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 280 mg of methyl 3-[(6R,8S)-2,2,3,3,6,9,9-heptamethyl-8-oxo-4-oxa-8λ4-thia-7-aza-3-siladecan-6-yl]benzoate.

Provenance & Evidence