4-Methylmorpholine → HCID 86612118, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[(tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid (5.89 g, 25.68 mmol) in CH2Cl2 (25 mL) were added dimethylhydroxylamine hydrochloride (2.51 g, 25.68 mmol) and N-methylmorpholine (2.82 mL, 25.68 mmol), sequentially. The mixture was cooled to 0° C., treated with 1.0M DCC in CH2Cl2, and stirred under an atmosphere of nitrogen while warning to room temperature overnight. The mixture was filtered, washing with CH2Cl2, and the resulting filtrate was concentrated in vacuo to afford an oil. The oil was re-suspended in EtOAc, and the mixture was filtered once more. The resulting filtered was subjected to column chromatography eluting with a gradient of 0-100% EtOAc/hexanes. Collection and concentration of the appropriate fractions afforded the product as an opaque white solid.

Provenance & Evidence