Triethylamine → Tert-butyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

Participants

Reaction Steps

A solution of 1-(1,1-dimethylethyl) 4-(4-hydroxymethyl-2-thiazolyl)-1-piperidinecarboxylate (i.e. the product of Example 1, Step B) (0.83 g, 2.8 mmol) and triethylamine (836 μL, 6.0 mmol) in dichloromethane (3 mL) was cooled to 0° C., and a solution of methanesulfonyl chloride (235 μL, 3.0 mmol) in dichloromethane (2 mL) was added dropwise. The reaction mixture was warmed to ambient temperature, stirred for 2 h, diluted with dichloromethane, washed with 1 N aqueous hydrochloric acid and brine, and dried (MgSO4). The organic layers were concentrated under reduced pressure and purified by silica gel chromatography using 25-50% ethyl acetate in hexanes as eluant to give 0.20 g of the title compound as a white solid.

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