Acetonitrile → 3-[2-(4-{2-Phenoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidine-3-ol

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Reaction Steps

Using a similar procedure to that described in Example 10, but using 1-(4-bromo-2,6-dimethylphenoxy)-2-phenoxyethanol as starting material in place of 1-(4-bromo-2,6-dimethylphenoxy)-2-methoxyethane and extracting the aqueous mixture obtained after diluting the reaction mixture with 2M aqueous sodium hydroxide with dichloromethane instead of diethyl ether, there was obtained 3-[2-(4-{2-phenoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidine-3-ol (28% yield) as a solid, m.p. 141-142° C. (after recrystallisation from acetonitrile); microanalysis, found: C, 76.2; H, 7.4; N, 3.5%; C25H29NO3 requires: C, 76.7, H, 7.5; N, 3.6%; in 28% yield NMR ([CD3 ]2O): 1.2-1.4(1H,m), 1.5-1.65(1H,m), 1.7-2.0(3H,m), 2.15-2.3(6H,s), 2.6-2.75(4H,t), 2.75-2.9(1H,d), 2.95-3.1(1H,d), 4.0-4.3(4H,m), 5.5(1H,s), 6.9-7.05(3H,m), 7.1(2H,s) and 7.25-7.4(2H,m); m/z 392 (M+H).

Provenance & Evidence