Diisopropylamine → HCID 67037408, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (15% solution in n-hexane; 9.5 mL, 0.022 mol) is added to a stirred solution of diisopropyl amine (3.1 mL, 0.022 mol) in tetrahydrofuran (15 mL) at −70° C. under an atmosphere of nitrogen and stirred for 30 minutes. A solution of piperidine-1,4-dicarboxylic acid-1-tert-butyl ester-4-ethyl ester (3 g, 0.012 mol) in tetrahydrofuran (10 mL) is introduced at −70° C. Hexamethyl phosphoramide (4.8 mL) is added and reaction mixture is allowed to stir till the temperature reaches at −45° C. Reaction mixture again cooled to −70° C., benzyl chloromethyl ether (5 mL, 0.035 mol) is added and stirred for 1 hour. Saturated aqueous solution of ammonium chloride (30 mL) is added slowly into the reaction mixture at −30° C. and stirred for 10 minutes. It is extracted with ethyl acetate (2×20 mL). Combined organic layer is dried over sodium sulfate. Removal of solvent under reduced pressure gives a viscous liquid which is purified by column chromatography (silica gel 230-400, toluene:ethyl acetate, 23:2 to furnish 4-benzyloxymethylpiperidine-1,4-dicarboxylic acid-1-tert-butyl ester-4-ethyl ester.

Provenance & Evidence