Heptane → N-[2-cyclopropyl-1-methyl-1-(5-methylthiazol-2-yl)ethyl]-2-methyl-propane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

A 2.0M solution of lithium diisopropylamide in THF (745 μl, 1.49 mmol) was added dropwise to a solution of 5-methylthiazole (148 mg, 1.49 mmol) in dry THF (0.5 ml) cooled to −78° C. and once the addition was complete the reaction was stirred for 30 minutes at −78° C. followed by addition of dry toluene (1.5 ml). To a solution of (NE)-N-(2-cyclopropyl-1-methyl-ethylidene)-2-methyl-propane-2-sulfinamide (CAN 1426426-70-1, 150 mg, 745 μmol) in dry toluene (1.5 mL) was added a 2.0M solution of trimethylaluminum in heptane (410 μl, 820 μmol). The previous solution was then added to the reaction mixture cooled at −78° C. The reaction was allowed to warm up to room temperature overnight. The reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride and was then diluted with ethyl acetate. The bi-phasic mixture was poured into a separatory funnel and extracted. The organic phase was collected, 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 (123 mg, 55%). MS (ESI, m/z): 301.4 (M+H+).

Provenance & Evidence