Diiodomethane → HCID 66734076, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of 1M diethylzinc in hexane (37.0 ml; 37.000 mmol) in anhydrous DCM (40 ml) was added dropwise a solution of TFA (2.82 ml; 36.924 mmol) in anhydrous DCM (20 ml). After 30 min., a solution of methylene iodide (2.97 ml; 36.924 mmol) in anhydrous DCM (20 ml) was added dropwise to the reaction mixture, and stirring at 0° C. was continued for 10 min. A solution of 3-methyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-1-vinyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (0.536 g; 1.231 mmol) in anhydrous DCM (5 ml) was then added dropwise, and the resulting mixture was further stirred at 0° C. for 1 h, and finally at rt for 6 h. The reaction mixture was then treated dropwise with TEA (7 ml), and with an aq. sat. solution of NaHCO3 (50 ml). The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH/25% aq. NH4OH, 200/10/1) afforded the target compound 1-cyclopropyl-3-methyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine as a yellow solid (0.186 g; 34%). LC-MS: tR=0.68 min.; [M+H]+=350.42 g/mol.

Provenance & Evidence