Lithium Hydroxide → HCID 66731651, compound

Participants

Reaction Steps

To a solution of methyl 2-benzylpiperidine-4-carboxylate (7.36 g, 31.55 mmol) and DIPEA (11.02 mL, 63.09 mmol) in DCM (200 mL) was added methyl chloroformate (3.18 mL, 41.01 mmol) in 100 mL DCM over 1 h. The reaction mixture was stirred for 40 min, then washed with satd NaHCO3, dried using a phase separator and evaporated. The residue was dissolved in THF (80 mL) followed by addition of LiOH (1.0 g, 42.0 mmol), MeOH (60 mL) and water (60 mL). The reaction mixture was stirred at room temperature under nitrogen atmosphere for 72 h. After evaporation of solvents, the residue was taken up in water. The pH was adjusted to <2 by addition of HCl (10%). The aqueous phase was then extracted with DCM (×5). The combined organic layers were dried by using a phase separator and evaporated to give 2-benzyl-1-(methoxycarbonyl)piperidine-4-carboxylic acid as an oil. MS m/z 276 (M−H)−.

Provenance & Evidence