Water → 4-(3-Methanesulfonyloxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

A solution of 3.34 g (13.96 mmol) of 4-(3-Hydroxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester in 100 ml CH2Cl2 was treated at 0° C. with 1.2 ml (15.4 mmol) of methanesulfonylchloride, 1.7 ml (20.93 mmol) of pyridine and 1.71 g (13.96 mmol) of DMAP. The reaction mixture was warmed up to RT for 3 h, treated with water (10 ml) and stirred for 5 min. After extraction with aqueous 10% KHSO4/Et2O (3×), the organic phases were washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 4.05 g (90%) of 4-(3-Methanesulfonyloxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester, MS: 317 (M).

Provenance & Evidence