Methanol → 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyl lithium (100 ml of a 2M solution in pentane) was added portion-vise over a period of 20 minutes to a stirred solution of ethynyltrimethylsilane (19.6 g) in dry tetrahydrofuran (400 ml) at -70° C. The mixture was stirred for 1 hour at -70° C. A solution of 3-quinuclidinone (2.4 g) in dry tetrahydrofuran (100 ml) was then added to the mixture and the mixture stirred for 1 hour at -70° C. Methanol (1 ml) was then added to the mixture and the mixture allowed to warm to room temperature. The solvents were removed by evaporation. Methanol (500 ml) and potassium carbonate (40 g) were added to the residue and the mixture was stirred for 1 hour. The solvent was removed by evaporation. The residue was triturated with water (500 ml) and then dried in vacuo to give 3-ethynyl-3-hydroxy-quinuclidine as a solid, m.p. 193-197° C.; NMR (DMSO-d6): 1.5-1.3(1H, m), 1.4-1.6(1H, m), 1.7-1.95(3H, m), 2.55-2.8(5H, m), 2.95(1H, d), 3.3(1H, d) and 5.4(1H, s); m/z 152 (M+H).

Provenance & Evidence