Diiodomethane → HCID 67490804, compound

Participants

Reaction Steps

To a solution of diethyl zinc (1M hexane solution, 22.3 ml) in dichloromethane (75 mL) was added dropwise diiodomethane (1.79 mL, 22.3 mmol) at −10° C., and the mixture was stirred for 15 min at the same temperature. A solution of (S)-6-oxo-5-[(R)-1-phenylethyl]-5,6-dihydro-4H-furo[3,4-c]pyrrole-3a-carboxylic acid tert-butyl ester in dichloromethane was added at −10° C., and the resulting mixture was stirred for 8 h at room temperature. The reaction mixture was quenched with 10% aq. citric acid. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with sat. aq. NaHCO3 and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 30% AcOEt in hexane to afford the title compound (1.96 g) as a white solid.

Provenance & Evidence