Trifluoroacetic acid → HCID 44467324, compound

Participants

Reaction Steps

Trifluoroacetic acid (0.5 mL) was added to a solution of 4-[(1H-indol-5-yl)-(3-methoxycarbonyl-benzyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (210 mg, 0.453 mmol) in DCM (2.0 mL). The reaction mixture was stirred for 3 hours, the solvent was then evaporated under reduced pressure and the residue was dissolved in DCM, a mixture of MeOH/NH4OH (9.5/0.5) was then added. The resulting mixture was filtered through a celite and silica pad and the filtrate was evaporated under reduced pressure. The residue was dissolved in THF (5.0 mL) and a solution of lithium aluminum hydride (1.0 M in THF, 1.81 mL, 1.81 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 30 minutes and it was then quenched by addition of Na2SO4.10H2O. The resulting mixture was filtered and the filtrate was evaporated under reduced pressure to give 13.2 mg (9% yield) of (3-{[(1H-indol-5-yl)-piperidin-4-yl-amino]-methyl}-phenyl)-methanol, MS=336 [M+H]+.

Provenance & Evidence