HCID 67740377, compound → HCID 67850599, compound

Participants

Reaction Steps

A mixture of 3-[2-{4-(2-methoxyethoxy)phenyl}ethynyl]-quinuclidin-3-ol (1.8 g) in ethanol (200 ml) and a catalyst of 10% (v/v) palladium on carbon (100 mg) was stirred under an atmosphere of hydrogen until hydrogen uptake ceased. The palladium/carbon catalyst was removed by filtration and the filtrate was evaporated. The residue was crystallised from a 3:1 (v/v) mixture of cyclohexane ethylacetate to give 3-[2-{4-(2-methoxyethoxy)phenyl}ethyl]quinuclidin-3-ol (700 mg) as a solid, mpt 116-117° C. Microanalysis, found C,71.1; H,9.2; N,4.5%; C18H27NO3 requires: C,70.8; H,8.9; N,4.59%; NMR ([CD3 ]2SO): 1.15-1.35 (1H, m), 1.4-1.6 (1H, m), 1.65-1.78 (2H, m), 1.9-2.08 (1H, m), 2.45-2.8 (10H, m), 3.3 (3H, s), 3.6-3.68 (2H, m), 4.0-4.08 (2H, m), 4.3 (1H, br), 6.78-6.86 (2H, d), 7.05-7.13 (2H, d); m/z 306 (M+H).

Provenance & Evidence