Methanol → N-(1-cyclopropylpropan-2-yl)-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

A 25 mL round-bottomed flask was charged with 2-methyl-propane-2-sulfinic acid [2-cyclopropyl-1-methyl-eth-(E)-ylidene]-amide (120 mg, 0.596 mmol) and dichloromethane (2 ml) under an argon atmosphere. The reaction mixture was cooled in a −78° C. bath. DIBAL-H (0.80 ml, 0.800 mmol) was added slowly dropwise. The reaction mixture was allowed to stir for 45 min after which the cooling bath was removed. The reaction mixture was stirred for 15 min at room temperature, after which the reaction mixture was returned to the cooling bath. The reaction was quenched with MeOH (0.08 mL, 1.98 mmol). The reaction mixture was diluted with dichloromethane (8 mL) and 1.0 M aqueous Na+K+ tartrate solution (5 mL). After stirring at room temperature overnight, the mixture was extracted with dichloromethane. The organic layer was concentrated to afford 50 mg of 2-methyl-propane-2-sulfinic acid (2-cyclopropyl-1-methyl-ethyl)-amide which was used in the next step directly without purification.

Provenance & Evidence