Sodium Bicarbonate → Racemic tert-Butyl-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Participants

Reaction Steps

A solution of tert-butyl-3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate (1.6 g, 3.5 mmol) in dichloromethane (87 mL) at 0° C. is treated with 1-chloro-N,N,2-trimethylpropenylamine (0.94 mg, 7.0 mmol). The mixture is allowed to warm to room temperature and stirred for 4 hours under nitrogen. Saturated sodium bicarbonate is added and the solution extracted with dichloromethane. The combined organic layers are dried over sodium sulfate, filtered, and concentrated to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound, which is used without further purification (1.6 g, 104%). ES/MS (m/e): 438 (M+H).

Provenance & Evidence