Dimethylformamide → HCID 67740281, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 2-allyl-4-bromophenoxyacetate (912 mg), 3-ethynyl-3-hydroxyquinuclidine (453 mg), bis (triphenylphosphine)-palladium (II) chloride (106 mg), copper (I) iodide (53 mg), triethylamine (3 ml) and dimethylformamide (6 ml) was stirred at 80° C. under an atmosphere of argon for 8 hours. The reaction mixture was cooled to ambient temperature and water (100 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts were combined and filtered. The filtrate was washed with saturated brine solution (3×50 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography on Alumina (Fluka 507C) using ethyl acetate containing 2.5% methanol as eluent to give 3-[2-(3-allyl-4-ethoxycarbonylmethyloxyphenyl)ethynyl]quinuclidin-3-ol (220 mg) as a solid, mp 95.9° C.; microanalysis, found: C, 70.7; H, 7.30; N, 3.50%; C22H27NO4.0.25 H2O requires: C, 70.6; H, 7.35; H, 3.72%; NMR (CDCl3): 1.28 (3H, t), 1.34-1.47 (1H, m), 1.52-1.72 (1H, m), 1.90-2.25 (3H, m), 2.25-2.60 (1H, m), 2.62-2.92 (4H, m), 2.97-3.09 (IH, d), 3.25-3.35 (1H, d of d), 3.42 (2H, d), 4.26 (2H, q), 4.62 (2H, s), 5.02-5.15 (2H, m), 5.88-6.08 (1H, m), 6.60-6.68 (1H, m) and 7.17-7.27 (2H, m); m/z 370 (M+H).

Provenance & Evidence