Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylate → 1-Azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol

Participants

Reaction Steps

A solution of 2-thienyllithium (1.0 M in THF, 13.0 mL, 13 mmol) was chilled down to −30° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.77 g, 4.20 mmol) in THF (12 mL) was slowly added to the 2-thienyllithium at −30° C. over 40 min. The reaction was allowed to warm up to room temperature for overnight. The reaction was quenched with H2O and then diluted with EtOAC, hexane and DCM causing a solid to crash out of solution. The solid was filtered off, resulting in the desired compound (0.9132 g, 71.3%). EI-MS m/z 306(M+) Rt (1.33 min).

Provenance & Evidence