1,2,3,4-Tetrahydroisoquinoline → HCID 59909766, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate (Preparation 3) (300 mg, 0.76 mmol) in ethanol (4 ml) was treated with 1,2,3,4-tetrahydroisoquinoline (0.95 ml, 7.60 mmol) and the resulting mixture was heated at 60° C. under a nitrogen atmosphere for 9 hours. The mixture was cooled and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:ethyl acetate (80:20). The residue was further purified by column chromatography on silica gel eluting with a gradient system of pentane:ethyl acetate (90:10) gradually changing to pentane:ethyl acetate (70:30) to afford the title compound (343 mg).

Provenance & Evidence