Trifluoroacetic acid → alpha-Methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic Acid

Participants

Reaction Conditions

Reaction Steps

TFA (10.0 mL) is added to a solution of tert-butyl α-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (780 mg, 2.09 mmol) and CH2Cl2 (10 mL) at 0° C. The solution is stirred for 2.5 hours at 0° C. and 1.5 hours at room temperature. After concentration, the residue is partitioned between EtOAc and water. The organic layer is extracted several times with 10% NaOH, the combined basic layers acidified (4N HCl), and the acidic layers extracted several times with CH2Cl2. The CH2Cl2 layers are dried (MgSO4), filtered, and concentrated to provide 79 mg (12%) of the title compound as a white solid (mp 94°-95° C.).

Provenance & Evidence