(+-)-3-Quinuclidinol → HCID 23295014, compound

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Reaction Steps

The title compound was prepared in an analogous manner to that in Example 36. 1-(4-Bromophenyl)cyclobutanecarbonyl chloride, prepared from the compound prepared in Example 10, was refluxed with 3-quinuclidinol overnight. The crude was chromatographed on silica gel using EtOAc-Et3N 90:10 as eluent. The yield was 0.46 g (19%); mp 222-226° C.; 1H NMR (CD3OD) δ 1.73 (m, 2H), 1.82-2.15 (m, 4H), 2.23 (br, 1H), 2.53 (m, 2H), 2.85 (m, 2H), 2.95-3.10 (m, 2H), 3.20-3.35 (m, 3H), 3.66 (m, 1H), 5.06 (m, 1H), 7.25 (d, 2H), 7.50 (d, 2H). Anal. (C18H22BrNO2.HCl) C, H, N.

Provenance & Evidence