2-(Benzenesulfonyl)-3-phenyloxaziridine → Benzyl 2-cyclopentyl-2-hydroxyacetate

Temperature

-78 °C

A 0.5 M potassium bistrimethylsilylamide-toluene solution (67.2 mL, 33.6 mmol) was added to anhydrous tetrahydrofuran (30 mL), and the mixture was cooled to −78° C. under nitrogen stream. To this mixture was added dropwise a solution of benzyl cyclopentylacetate (6.11 g, 28 mmol) in anhydrous tetrahydrofuran (30 mL) over 1 h. After the mixture was stirred at −78° C. for 30 min, a solution of Davis oxaziridine reagent (8.78 g, 33.6 mmol) in anhydrous tetrahydrofuran (30 mL) was added dropwise over 1 h. The reaction mixture, which had been stirred at −78° C. for 1 h, was diluted with a saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the organic solvent in the filtrate was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate 9:1) to give 6.157 g of benzyl 2-cyclopentyl-2-hydroxyacetate (yield: 94%).

1. stirringThe reaction mixture, which had been stirred at −78° C. for 1 h
2. extractionextracted with diethyl ether
3. washThe organic layer was washed with water and brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customthe organic solvent in the filtrate was evaporated under reduced pressure

ORD record

ord-bfd4637e529943f19a72c02b38b47a8a

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260375B2