Triethylamine → Methanesulfonic acid 2-(2,5-dimethoxy-phenyl)-cyclopentylmethyl ester

Participants

Reaction Conditions

Reaction Steps

Dissolve [2-(2,5-dimethoxy-phenyl)-cyclopentyl]-methanol (3.6 g, 15 mmol) in dichloromethane (94 ml), add 2,6-dimethylaminopyridine (0.4 g, 0.31 mmol), add triethylamine (4.7 ml, 33.5 mmol), cool to 0° C., add methanesulfonyl chloride (1.9 g, 17 mmol), remove ice bath and stir 2 hours at room temperature. Quench with water and ethyl acetate, separate layers, wash with brine, dry and concentrate to give the title compound (4.8 g, 100%): 1H NMR (CDCl3) δ 6.78-6.69 (m, 3H), 3.86-3.82 (m, 1H), 3.79 (s, 3H), 3.76 (s, 3H), 3.68-3.64 (m,1H), 3.53-3.47 (m, 1H), 2.83-2.76 (m, 1H), 2.69 (s,3H), 1.97-1.88 (m, 3H), 1.67-1.60 (m,3H).

Provenance & Evidence