Tetrahydrofuran → (S)-N-((2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-(tetrahydrofuran-3-yl)butan-2-yl)-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

A solution of azeotropically dried (S,E)-N—((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (2.3 g, 5 mmol) and 3-(iodomethyl)-THF (1 g, 7 mmol) in dry THF (10 mL) was brought to −78° C. followed by the dropwise addition of tert-butyllithium (6 mL, 11 mmol). A white precipitate was formed. The resulting solution was stirred at −78° C. for 40 min, quenched with sat NH4Cl and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, concentrated, and chromatographed on silica gel using 0-5% EtOAc/hexanes to afford a colorless oil as (S)—N-((2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-(tetrahydrofuran-3-yl)butan-2-yl)-2-methylpropane-2-sulfinamide.

Provenance & Evidence