Pyrrolidine → HCID 86598342, compound

Participants

Reaction Steps

A mixture of (3R,9aR)-2-[3,5-bis(trifluoromethyl)benzoyl]-3-(1H-indol-3-ylmethyl)-octahydro-2H-pyrido[1,2-a]pyrazin-7-one (0.785 g, see example 3 steps 1–7), pyrrolidine (0.107 g), acetic acid (0.09 g) and sodium triacetoxyborohydride (0.47 g) in 1,2-dichloroethane (60 mL) was stirred for three days at room temperature. The resulting mixture was poured into water, basified with sodium bicarbonate (5% aq. soln.) and extracted with dichloromethane. The organic layer was concentrated and the residue was purified by column chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92:7.5:0.5) to afford 3,5-bis(trifluoromethyl)phenyl-[(3R,7R,9aR)-3-(1H-indol-3-ylmethyl)-7-pyrrolidin-1-yl-octahydropyrido[1,2-a]pyrazin-2-yl]-methanone (0.20 g, Rf 0.23 (CH2Cl2/MeOH/NH4OH 92:7.5:0.5)) (compound 24) and 3,5-bis(trifluoromethyl)-phenyl-[(3R,7S,9aR)-3-(1H-indol-3-ylmethyl)-7-pyrrolidin-1-yl-octahydropyrido[1,2-a]pyrazin-2-yl]-methanone (0.48 g, Rf 0.15 (CH2Cl2/MeOH/NH4OH 92:7.5:0.5)) (compound 25).

Provenance & Evidence