Acetic Acid → (R)-3-[2-((S)-1-Aminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester

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Reaction Steps

A mixture of (R)-3-[2-((S)-1-benzyloxycarbonylaminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester (2.75 g, 5.75 mmol) 10% Pd/C (275 mg) and AcOH (4 mL) in EtOAc (40 mL) was purged with a stream of nitrogen and then was stirred at RT for 20 h under an hydrogen atmosphere. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) affording (R)-3-[2-((S)-1-Aminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester as a white foam (1.65 g, 83%). LCMS: RT 2.30 min [M+H-tBu]+ 289.2.

Provenance & Evidence