Triethylamine → Methanesulfonic acid 1-pyridin-2-yl-cyclopentylmethyl ester

Participants

Reaction Steps

To a stirred solution of (1-pyridin-2-yl-cyclopentyl)-methanol (432) (1.8 g, 10.169 mmol) in dichloromethane (20 mL), triethylamine (2.827 mL, 20.339 mmol) and mesylchloride (0.94 mL, 12.203 mmol) were added at 0° C. The reaction mixture was allowed to stir for 2 h at room temperature while silica thin layer chromatography was performed (50% ethyl acetate in hexane; Rf=0.6) The reaction was quenched with water (30 mL) and extracted with dichloromethane (2×70 mL). The organic part was dried and concentrated. The resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 25% ethyl acetate in hexane as eluent to get methanesulfonic acid 1-pyridin-2-yl-cyclopentylmethyl ester (433) (2.05 g, 79%) as a white solid.

Provenance & Evidence