3-Fluorobenzylamine → Tert-butyl 2-(4-(3-fluoro-2-methylbenzylcarbamoyl)-4-(hydroxymethyl)piperidin-1-yl)-2-oxoethylcarbamate

Participants

Reaction Steps

To a solution of crude 1-(2-(tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid (120 mg, ˜0.379 mmol, 1.0 equiv) in DMF (30 mL) were added HBTU (144 mg, 0.379 mmol, 1.0 equiv.), 2-methyl, 3-fluorobenzylamine (53 mg, 0.379 mmol, 1.0 equiv.) and DIEA (132 μL, 0.758 mmol, 2.0 equiv.). The reaction mixture was stirred overnight at rt. The mixture was partitioned between EtOAc and H2O. The organic layer was washed by 1 N HCl, Saturated NaHCO3, water and brine, dried over Na2SO4, and concentrated to dryness to give tert-butyl 2-(4-(3-fluoro-2-methylbenzylcarbamoyl)-4-(hydroxymethyl)piperidin-1-yl)-2-oxoethylcarbamate (185 mg), which was used without further purification. LRMS (M+H+) m/z 439.1.

Provenance & Evidence