Water → HCID 69819839, compound

Participants

Reaction Conditions

Reaction Steps

(4R,8aS)-4-Benzhydryl-2-(2-methoxy-5-bromobenzyl)octahydropyrrolo[1,2-a]pyrazine dihydrochloride (29.8 mg) was dissolved in a mixture of 1,2-dimethoxyethane (0.5 ml) and 2M aqueous sodium carbonate (0.16 ml). Then phenylboronic acid (9.01 mg) and tetrakis(triphenylphosphine)palladium (6.1 mg) were added to the solution at room temperature. The whole was stirred for 2 hours at 85° C. The reaction mixture was poured into water, extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by preparative TLC (0.5 mm) with a mixture of dichloromethane and methanol (15:1) as an eluent, and treated with 4N hydrogen chloride in ethyl acetate to give (4R,8aS)-4-benzhydryl-2-[(4-methoxy-[1,1′-biphenyl]-3-yl)methyl]octahydropyrrolo[1,2-a]pyrazine dihydrochloride (24.4 mg) as a brownish power.

Provenance & Evidence