Lithium tri-s-butylborohydride → 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (93 mg, 0.29 mmol) in tetrahydrofurane (5 mL) was added L-selectride (1 M in THF, 0.58 mL, 0.58 mmol) dropwise at −78° C. The reaction was stirred for 2.5 h at −78° C. The reaction mixture was quenched with sat. ammonium chloride solution (100 mL), and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×10 ml). The organic layers were combined, washed with brine (10 ml), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to yield 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]-amide (80 mg, 86%) as an oil. Major diastereomer was 96.4% de by HPLC.

Provenance & Evidence