Trifluoroacetic acid → HCID 11261756, compound

Participants

Reaction Conditions

Reaction Steps

To mixture of anisole (35 mg), (3R,9aR)-3-[2-(3,5-bis(trifluoromethyl)-benzoyl)-7-pyridin-4-yl-1,3,4,6,9,9a-hexahydro-2H-pyrido[1,2-a]pyrazin-3-ylmethyl]-indole-1-carboxylic acid tert-butyl ester and (3R,9aR)-3-[2-(3,5-bis(trifluoromethyl)-benzoyl)-7-pyridin-4-yl-1,3,4,8,9,9a-hexahydro-2H-pyrido[1,2-a]pyrazin-3-ylmethyl]-indole-1-carboxylic acid tert-butyl ester (0.20 g) in dichloromethane (2 ml) was added trifluoroacetic acid, at 0° C. After 1.5 h at room temperature the mixture was diluted with dichloromethane, quenched with ice, and carefully basified with ammonium hydroxide. The layers were separated, the organic layer dried filtered and concentrated in vacuo. The residue was dissolved in methanol and heated at 50° C. for 1 h, then cooled to room temperature and concentrated in vacuo. The residual solid was stirred with hexanes overnight and then collected by filtration to afford (3R,9aR)-(3,5-bis(trifluoromethyl)phenyl)-[3-(1H-indol-3-ylmethyl)-7-pyridin-4-yl-1,3,4,8,9,9a-hexahydro-pyrido[1,2-a]pyrazin-2-yl]-methanone (compound 1) (70 mg). Rf 0.51 (SiO2, CH2Cl2/MeOH/NH4OH 93:7:0.5).

Provenance & Evidence