Diiodomethane → HCID 67490804, compound

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.

1. stirringthe resulting mixture was stirred for 8 h at room temperature
2. customThe reaction mixture was quenched with 10% aq. citric acid
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with dichloromethane
5. washThe combined organic layers were washed with sat. aq. NaHCO3 and brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel chromatography
9. washeluting with 30% AcOEt in hexane

ORD record

ord-7f40e8a59a08461b9c1238e992842044

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2