Sodium Methoxide → HCID 68795785, compound

Participants

Reaction Steps

A mixture of (3R,4R)-4-o-tolyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (200 mg) and sodium methoxide (65 mg) in anhydrous toluene (6 mL) was heated at reflux over night. After cooling to room temperature the reaction mixture was quenched with water and concentrated in vacuo. The residue was dissolved in a mixture of 1,4-dioxane (3 mL) and 2 M aqueous sodium hydroxide solution (3 mL). After stirring at RT for 5 h the mixture was diluted with water and washed with two portions of tert-butyl methyl ether. The aqueous layer was cooled to 0° C., acidified to pH 1-2 with ice-cold 1 M aqueous KHSO4 solution and extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and evaporated to give (3S,4R)-4-o-tolyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester as a white solid, MS: 318.4 ([M−H])−.

Provenance & Evidence