Methanol → HCID 67740237, compound

Participants

Reaction Steps

3-[2-(2-formyl-4-(2-methoxycarbonylethyl)phenyl]ethynyl]quinuclidin-3-ol (575 mg) was stirred with methanol (25 ml) at ambient temperature under an atmosphere of argon. Sodium borohydride (329 mg) was added portionwise over 5 minutes to the reaction mixture and stirring continued at ambient temperature overnight. Water (25 ml) was added and the mixture was extracted with ethyl acetate (25 ml). The organic phase was separated, washed with saturated aqueous sodium carbonate (3×25 ml), water (3×25 ml), dried (MgSO4) and evaporated. The residue was purified by elution through silica gel (10 g Bond elut column) with a gradient of 0-30% methanol in dichloromethane to give 3-[2-(2-hydroxymethyl-4-(2-methoxycarbonylethyl)phenyl)ethynyl]quinuclidin-3-ol (160 mg) as a solid, m.p. 35.8° C.; microanalysis, found: C, 69.2; H, 7.5; N, 3.9% C20H25NO4 0.2 H2O requires: C, 69.2; H, 7.38; N, 4.04%; NMR(CDCl3): 1.4(1H,m), 1.66(1H,m), 2.02(3H,m), 2.62(2H,t), 2.8(3H,m), 2.95(2H,t), 3.03(1H,d), 3.27(1H,d), 3.66(3H,s), 4.75(2H,s), 7.07(1H,m) and 7.3(2H,m); m/z 344 (M+H).

Provenance & Evidence