tert-Butylsulfinamide, (R)-(+)- → (NZ)-2-methyl-N-[1-(2-methylsulfonyl-1,3-thiazol-5-yl)propylidene]propane-2-sulfinamide

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Reaction Steps

A mixture of crude 1-(2-methanesulfonyl-thiazol-5-yl)-propan-1-one (110 mg, 0.50 mmol), (R)-2-methyl-2-propanesulfinamide (70 mg, 0.55 mmol) and titanium isopropoxide (0.29 mL, 1.00 mmol) in tetrahydrofurane (10 mL) was warmed to reflux for 18 h. The mixture was cooled to room temperature and diluted with diethylether (100 mL) and water (6 mL). The mixture was stirred for 10 min and then dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 0-100% ethyl acetate in hexanes to give 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (93 mg, 58%). Unreacted 1-(2-Methanesulfonyl-thiazol-5-yl)-propan-1-one (43 mg, 39%) was also isolated.

Provenance & Evidence