Hydrochloric Acid → Tert-butyl 4-(2-chlorobenzylcarbamoyl)-4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-tert-butyl 4-methyl 4-(2-chlorobenzylcarbamoyl)piperidine-1,4-dicarboxylate (2.8 g, 6.8 mmol) in THF (20 mL) and CH3OH (10 mL) was added lithium borohydride (1.4 g, 68 mmol, 10 equiv.). The reaction mixture was stirred for 3 h and neutralized with HCl (1N). The residue was partitioned between EtOAc and H2O. The organic layer was dried over Na2SO4 and concentrated to purify on RP-HPLC using a mixture of acetonitrile and H2O to give tert-butyl 4-(2-chlorobenzylcarbamoyl)-4-(hydroxymethyl)piperidine-1-carboxylate (2.2 g, 84%). LRMS (M-tBu+H+) m/z 327.0.

Provenance & Evidence