Methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate → Methyl 2-{4-[1-(tert-butoxycarbonyl)piperidin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

Participants

Reaction Steps

A solution of methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (228 mg, 0.493 mmol) in MeOH (5.0 mL) was degassed thoroughly and palladium on carbon (5% Pd/C, 15.6 mg, 0.0025 mmol) was added. The mixture was stirred at rt under an atmosphere of hydrogen gas for 2 h. The reaction mixture was filtered through a pad of Celite, and the filtrate was concentrated to give methyl 2-{4-[1-(tert-butoxycarbonyl)piperidin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (200 mg, 87%) which was used without purification. LC-MS: (FA) ES+ 465.

Provenance & Evidence