Trimethylsilyl triflate → HCID 86690105, compound

Temperature

-78 °C

To a solution of ethyl 5-oxooctahydropentalene-2-carboxylate (210 mg) in DCM (5 mL) cooled to −78° C. were added slowly trimethylsilyl trifluoromethanesulfonate (11.89 mg, 0.054 mmol) and 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (287 mg, 1.391 mmol) under nitrogen. After stirring at −78° C. for 30 min, the reaction mixture was warmed to rt and stirred at rt for 16 h. The reaction was quenched with anhydrous pyridine at −78° C. followed by sat. NaHCO3, and then extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography to afford ethyl hexahydro-1′H-spiro[[1,3]dioxolane-2,2′-pentalene]-5′-carboxylate (a mixture of endo/exo isomers) as a clear oil.

1. temperaturethe reaction mixture was warmed to rt
2. stirringstirred at rt for 16 h
3. customThe reaction was quenched with anhydrous pyridine at −78° C.
4. extractionextracted with EtOAc
5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography

ORD record

ord-e79d6d27da3542bbb9b8e6cfad961f63

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09326973B2