tert-Butyl acetate → Tert-butyl 3-(tert-butylsulfinylamino)-3-cyclopropyl-butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl acetate (1.29 g, 1.48 ml, 11.1 mmol) in THF (20 ml) cooled to −78° C. was added a 2M solution of lithium diisopropylamine in THF/n-heptane (5.55 ml, 11.1 mmol) over 10 minutes. The reaction mixture was stirred for 40 minutes at −78° C. followed by addition of a solution of (E)-N-(1-cyclopropylethylidene)-2-methylpropane-2-sulfinamide (CAN 1426425-10-6, 1.6 g, 8.54 mmol) in THF (5 ml) to the reaction cooled at −78° C. The reaction was stirred at −78° C. for 90 minutes and then let to warm up to 0° C. After stirring 1 hour at 0° C. the reaction was quenched by addition of water. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (1.93 g, 75%). MS (ESI, m/z): 304.5 (M+H+).

Provenance & Evidence