Sodium Hydroxide → HCID 21472379, compound

Participants

Reaction Steps

To a solution of 3-[2-(4-ethoxycarbonylphenyl)ethynyl]-3-hydroxyquinuclidine (250 mg) in ethanol (20 ml) was added 4N aqueous sodium hydroxide solution (0.7 ml). The reaction mixture was stirred for 18 hours. The reaction mixture was evaporated and the residue was acidified with 5N hydrochloric acid. The mixture was evaporated to give a solid which was treated with methanol/ethyl acetate to give 3-[2-(4-carboxyphenyl)ethynyl]-3-hydroxyquinuclidine (120 mg), m.p. 288°-290° C.; microanalysis, found: C, 59.4; H, 5.8; N, 4.1; Cl, 13.1%; C16H17NO3.0.5NaCl. 0.5HCl requires: C, 60.3; H, 5.53; N, 4.39; Cl, 11.1%; NMR: 1.66-1.82(1H,m), 1.86-2.31(4H,m), 3.03-3.45(5H,m), 3.51-3.63(1H,d), 6.55(1H,s), 7.54-7.62(2H,d), 7.89-7.98(2H,d), 12.1(1H,br); m/z 272(M+H).

Provenance & Evidence