2-(Benzenesulfonyl)-3-phenyloxaziridine → Benzyl 4-fluoro-1-hydroxycyclohex-3-ene-1-carboxylate

Temperature

-78 °C

A mixture of benzyl 4-fluorocyclohex-3-ene-1-carboxylate (1.77 g, 7.56 mmol) and 38 mL of THF was stirred vigorously and cooled to −78° C. To the reaction mixture was added dropwise over 15 minutes a solution of 0.5 M potassium bis(trimethylsilyl)amide in toluene (2.56 g, 12.8 mmol. The reaction mixture was allowed to stir vigorously for 1 hour. In a separate flask, 3-phenyl-2-(phenyl-sulfonyl)oxaziridine (2.17 g, 8.31 mmol) was dissolved in 2 mL of THF. The oxaziridine solution was then added to the reaction mixture dropwise. The reaction mixture was allowed to stir for 2 hours more and quenched with a saturated aqueous ammonium chloride solution. The biphasic reaction was separated and the aqueous layer was extracted three times with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered, concentrated and purified by chromatography on silica gel, eluting with 0-15% EtOAc in hexanes, to give benzyl 4-fluoro-1-hydroxycyclohex-3-ene-1-carboxylate as an oil.

1. stirringto stir vigorously for 1 hour
2. stirringto stir for 2 hours more
3. customquenched with a saturated aqueous ammonium chloride solution
4. customThe biphasic reaction
5. customwas separated
6. extractionthe aqueous layer was extracted three times with EtOAc
7. dry with materialThe combined organic extracts were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. custompurified by chromatography on silica gel
11. washeluting with 0-15% EtOAc in hexanes

ORD record

ord-7afb20c90d3d4bf3bbc1561d08f3b990

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816380B2