Sodium Methoxide → HCID 70358178, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 12.78 g (40 mmol) of 3-[N-(5-methoxybenzocyclobuten-1-ylmethyl)-N-(3-oxopropyl)-amino]-propionic acid ethyl ester in 100 ml of dimethylformamide is added to a solution of 2.43 g (45 mmol) of sodium methoxide in 15 ml of dimethylformamide and the whole is stirred for 3 hours at 40° C. The solvent is then evaporated off under reduced pressure and the residue is separated into its components by chromatography on 400 g of silica gel with dichloromethane/methanol (95:5). Trans-4-hydroxy-1-[(5-methoxybenzocyclobuten-1-yl)methyl]-piperidine-3-carboxylic acid ethyl ester is isolated first and then cis-4-hydroxy-1-[(5-methoxybenzocyclobuten-1-yl)methyl]-piperidine-3-carboxylic acid ethyl ester the hydrochloride of which has a melting point of 156°-160° C.

Provenance & Evidence