4-Methylmorpholine → HCID 11616671, compound

Participants

Reaction Conditions

Reaction Steps

21.5 g of t-butoxycarbonylproline are dissolved in 500 ml of methylene chloride. The solution is cooled to -70° C. 20.2 g of N-methylmorpholine are added, followed by the addition of 13.7 g of isobutylchloroformate. The reaction mixture is warmed up to -15° C. and again cooled to -70° C. 15.6 g of methyl serinate hydrochloride are added to the reaction mixture which is stirred for sixteen hours at room temperature. The reaction mixture is extracted three times with 1 M potassium bisulfate, three times with a saturated solution of potassium bicarbonate and two times with brine. The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and stripped of solvent. The product is purified by chromatography on silica gel to give methyl t-butoxycarbonylprolylserinate.

Provenance & Evidence