Methanol → HCID 66731865, compound

Participants

Reaction Steps

Dimethyl 2-(4-chlorobenzyl)piperidine-1,4-dicarboxylate (4.74 g, 14.55 mmol) was dissolved in tetrahydrofuran (15 mL) followed by addition of LiOH (0.430 g, 17.97 mmol), MeOH (10 mL) and water (10 mL). The reaction mixture was stirred at room temperature overnight. The solvents were evaporated and the residue was taken up in water. The pH was adjusted to <2 by addition of 2 M HCl. The product was poorly soluble and attempts to extract the aqueous phase with DCM and ethyl acetate failed. Instead the mixture was concentrated and then filtered, washed with water and dried to give a yellow solid material. The water phase did contain some product and was extracted with DCM (×3) and dried with a phase separator to give about 500 mg. Crude 2-(4-chlorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (4.27 g, quant.) was isolated. MS m/z 312, 314 (M+H)+

Provenance & Evidence