4-Methylmorpholine → O-Benzylhydroxylamine

Participants

Reaction Steps

CDI (162 mg) is added to a solution of α-[2-[[(4-methylphenyl)sulfonyl]amino]ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic acid (453 mg) and CH2Cl2 (5.0 mL). The solution is stirred for 1 hour at room temperature and then O-benzylhydroxylamine hydrochloride (192 mg) and 4-methylmorpholine (0.13 mL) are added. The solution is stirred for 16 h at room temperature. The solution is diluted with 60 mL of EtOAc which is washed with 10% HCl, brine, dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (1:1 hexane:EtOAc) provides a lactam intermediate with no evidence of O-benzylhydroxylamine incorporation:

Provenance & Evidence