Water → HCID 67851393, compound

Participants

Reaction Steps

A 1M solution of lithium aluminium hydride in tetrahydrofuran (10 ml) was added over a period of 20 minutes to a stirred solution of 3-[2-{4-(2-methoxyethoxy)phenyl}ethynyl]quinuclidin-3-ol (3.01 g) in dry tetrahydrofuran (100 ml) under an atmosphere of argon at 40° C. The reaction mixture was then stirred at ambient temperature for 16 hours. Water (0.4 ml) and 2M aqueous sodium hydroxide solution (0.8 ml) was then added to the reaction mixture dropwise followed by a further quantity of water (1.2 ml). The resulting precipitate was collected by filtration and the filtrate was evaporated. The residue from the filtrate was crystallised from acetonitrile to give 3-[(E)-2-{4-(2-methoxyethoxy)phenyl}vinyl]quinuclidin-3-ol (2.54 g) as a solid, mp 164-166° C., microanalysis, found C,71.4; H,8.6; N,4.5%; C18H25NO3 requires: C,71.3; H,8.31; N,4.62%; NMR ([CD3 ]2SO): 1.15-1.32 (1H, m), 1.38-1.52 (1H, m), 1.62-1.74 (2H, m), 1.95-2.1 (1H, m), 2.58-2.6 (5H, m), 2.82-2.92 (1H, d), 3.3 (3H, s), 3.6-3.67 (2H, m), 4.03-4.1 (2H, m), 4.66 (1H, s), 6.38-6.45 (1H, d, J=16.67), 6.51-6.58 (1H, d, J=16.67), 6.86-7.12 (2H, d) and 7.32-7.38 (2H, d); m/z 304 (M+H).

Provenance & Evidence