Methanol → HCID 69557998, compound

A solution of (+)-trans-1-hydroxymethyl-4-methylene-2-(3-fluorophenyl)cyclopentane from Step C (1.87 g, 9.0 mmol) in methanol (75 mL) was cooled in a dry ice/acetone bath and ozone was bubbled into the solution until the blue color persisted. The excess ozone was removed with a stream of nitrogen and then dimethylsulfide (5 mL) was added. After 10 min, the bath was removed and the reaction was allowed to warm to rt over 2 h. The mixture was treated with 10 drops of sulfuric acid (c) in water (2 mL) for 1 h before most of the methanol was removed in vacuo. The mixture was diluted with water and extracted twice with ethyl acetate and the organic layers were washed with brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC (50% ethyl acetate in hexanes) to give the title compound (1.87 g)), [α]D=+132 (MeOH, c=1.2).

1. customozone was bubbled into the solution until the blue color
2. customThe excess ozone was removed with a stream of nitrogen
3. additiondimethylsulfide (5 mL) was added
4. customthe bath was removed
5. additionThe mixture was treated with 10 drops of sulfuric acid (c) in water (2 mL) for 1 h before most of the methanol
6. customwas removed in vacuo
7. additionThe mixture was diluted with water
8. extractionextracted twice with ethyl acetate
9. washthe organic layers were washed with brine
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated
12. customThe residue was purified by FC (50% ethyl acetate in hexanes)

ORD record

ord-94d1bc172ed643158fd4736144fd5d6b

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06506777B1