Sodium Carbonate → HCID 69054774, compound

Participants

Reaction Steps

To a stirred solution of 2,2,2-trichloroethyl 3-[(4-methoxyphenyl)sulfanyl]-8-azabicyclo[3.2.1]octane-8-carboxylate (Preparation 11, 52.7 g, 0.12 moles) in tetrahydrofuran under nitrogen was added zinc dust (20 g,) and potassium hydrogenphosphate (1 M, 125 ml). The reaction mixture was stirred for 2 h at room temperature before adding more zinc dust (30 g) followed by heating on a steam bath for 30 min. The reaction mixture was cooled to room temperature and diluted with water (1 l). Sodium carbonate was added to adjust the pH to 10. The reaction mixture was filtered and the filtrate was separated and then extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound as a yellow oil (26.0 g, 84%). The oil was purified by column chromatography on silica gel (350 g) eluting with methanol:dichloromethane:0.88 ammonia solution (10:90:1) to give the product as an oil which crystallised on standing (13 g, 42%). The solid was further purified by stirring in ether and filtering to give a light yellow solid (9 g, 29%).

Provenance & Evidence