Methanol → HCID 18686048, compound

A solution of 3-(S)-(benzyloxymethyl)-4-(R)-(3-fluorophenyl)-1-methylenecyclopentane (0.77 g, 2.75 mmol) from Step A in methanol (30 mL) was cooled to −70° C. and ozone was bubbled through the solution until a blue color persisted. The excess ozone was removed with a stream of nitrogen and then dimethyl sulfide (5 mL) was added and the reaction was allowed to warm to rt over 16 h. Several drops of 2N HCl were added and the solution was stirred for 15 min to convert any methyl ketal to the desired ketone. The methanol was removed in vacuo and the was residue diluted with water, aq. sodium bicarbonate and ether.). The layers were separated and the aqueous was extracted with ether. The organic layers were washed with water, then brine, dried over sodium sulfate and concentrated. The residue was purified by FC using 10% ethyl acetate in hexanes to afford the title compound (0.88 g).

1. customozone was bubbled through the solution until a blue color
2. customThe excess ozone was removed with a stream of nitrogen
3. additiondimethyl sulfide (5 mL) was added
4. additionSeveral drops of 2N HCl were added
5. customThe methanol was removed in vacuo
6. additionthe was residue diluted with water, aq. sodium bicarbonate and ether
7. customThe layers were separated
8. extractionthe aqueous was extracted with ether
9. washThe organic layers were washed with water
10. dry with materialbrine, dried over sodium sulfate
11. concentrationconcentrated
12. customThe residue was purified by FC

ORD record

ord-296d069d1da546deb031b3f8e3bb5ead

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06358979B1