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

Participants

Reaction Steps

To a chilled (−78° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (93 mg, 0.29 mmol) in THF (5 mL) is added a 1 M solution of lithium tri-sec-butylborohydride (L-Selectride) (0.58 mL, 0.58 mmol) in THF dropwise. After 2.5 hours, the reaction mixture is quenched with saturated aqueous ammonium chloride solution (100 mL), and the aqueous layer is separated. The aqueous layer is extracted with EtOAc (2×10 mL). The combined organic layers are washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting using a gradient of 0-100% EtOAc in hexanes to afford 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]-amide.

Provenance & Evidence