Water → HCID 86676357, compound

A solution of methylenebicyclo[2.2.1]heptan-1-yl trifluoromethanesulfonate (7.6 g, 0.03 mol) in methanol (100 mL) was cooled to −40° C. and an ozone stream was passed through the reaction mixture. When the color of the mixture turned to blue, the ozone was eliminated by passing a stream of argon through the solution for 10 min. Dimethyl sulfide (5 mL) was added to the mixture and the reaction mixture was allowed to warm to room temperature. The resulting mixture was poured into water and extracted with DCM (2×40 mL). The combined extracts were washed with brine (100 mL) and dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to give the desired product (4.6 g, 18.1 mmol, yield: 60%) as a yellowish oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.73 (brs, 1H), 2.44-2.34 (m, 2H), 2.26-2.13 (m, 4H), 2.06-2.02 (m, 1H), 1.70-1.66 (m, 1H).

1. customfor 10 min
2. extractionextracted with DCM (2×40 mL)
3. washThe combined extracts were washed with brine (100 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationThe solution was concentrated under reduced pressure
6. customto give the crude product, which
7. customwas purified by silica gel column chromatography (10% ethyl acetate in petroleum ether)

ORD record

ord-e58e3e97997c485cabba1d53ee5f0cd1

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139534B2