Tetrahydrofuran → Benzyl 2-cyclopentyl-2-hydroxyacetate

Temperature

-78 °C

A 1.0 M sodium hexamethyldisilazide solution in THF (27.5 ml, 27.5 mmol) was added to anhydrous THF (30 ml), and the mixture was cooled to −78° C. An anhydrous THF solution (20 ml) of benzyl cyclopentylacetate (5.0 g, 22.90 mmol) was added dropwise to the mixture over 30 min, and the mixture was stirred for additional 30 min. Subsequently, an anhydrous THF solution (20 ml) of n-benzyl-benzenesulfonyloxaziridine (7.18 g, 27.5 mmol) was added dropwise to the mixture at −78° C. over one hr, and the mixture was stirred for additional one hr. The reaction mixture was quenched with saturated ammonium chloride and was extracted with ether. The organic layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=94:6) to give the title compound as a light yellow oil (3.2 g, yield 60%).

1. stirringthe mixture was stirred for additional one hr
2. customThe reaction mixture was quenched with saturated ammonium chloride
3. extractionwas extracted with ether
4. washThe organic layer was washed with water and saturated brine
5. dry with materialwas dried over anhydrous magnesium sulfate
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=94:6)

ORD record

ord-d904b51e008f4721af8b233549606257

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115079B2