Hexachloroethane → HCID 66733744, compound

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) solution of 3-ethyl-1-iodo-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (300 mg; 0.546 mmol) in anhydrous THF (4 ml) was treated dropwise with a solution of 1.6M n-BuLi in hexanes (0.34 ml; 0.546 mmol). The resulting solution was additionally stirred at −78° C. for 10 min., and was then treated dropwise with a solution of hexachloroethane (517 mg; 2.184 mmol; 4 eq.) in anhydrous THF (1 ml). The reaction mixture was further stirred at −78° C. for 1 h. The mixture was then quenched with water (0.2 ml), diluted with ether (30 ml), and was allowed to warm-up to rt. The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=100/3) to give the pure product 1-chloro-3-ethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow solid (143 mg; 57%). LC-MS: tR=1.02 min.; [M+H]+=458.49 g/mol.

Provenance & Evidence