Sodium hydride → HCID 86742163, compound

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Reaction Steps

N-(4-Methoxy-1,4-dioxobutyl)-L-phenylalanine, methyl ester, 6.74 g (0.023 mole), was dissolved in 200 ml of dioxane, and 2.2 g (0.055 mole) of 60% sodium hydride in mineral oil dispersion slowly added. The mixture was refluxed for four hours, stirred, and allowed to reach room temperature overnight. The solvent was evaporated in vacuo and the residue dissolved in 100 ml of water, acidified with concentrated hydrochloric acid to pH 8.5 and extracted with 200 ml ethyl acetate. The ethyl acetate layer was separated, dried over sodium sulfate, evaporated in vacuo, and the residue chromatographed using 150 g of silica gel and eluting with 500 ml of dichloromethane-methanol (98:2) to give 3,6-dioxo-2-(phenylmethyl)-4-piperidinecarboxylic acid, methyl ester: (DL-mixture at 2 position), 5.1 g; mp 146°-147.5°.

Provenance & Evidence