Hydrogen Peroxide → (R)-alpha-(Hydroxymethyl)-cyclopentanepropanoic acid

Temperature

0 °C

(4S)-3-[(2R)-3-Cyclopentyl-2-(hydroxymethyl)propanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one (33.1 g, 0.1 mol) was stirred in a mixture of THF (330 mL) and water (55 mL) and cooled to 0° C. 30% Hydrogen peroxide (96 mL, 1 mol) was added, followed by lithium hydroxide monohydrate (8.4 g, 0.2 mol). The reaction was warmed to room temperature, and then stirred overnight. The THF was removed by rotary evaporation. The aqueous residue was washed with dichloromethane (3×100 mL), was acidified with 6N HCl, and was extracted with ethyl acetate (4×100 mL). The organic extracts were dried (MgSO4) and were evaporated to provide (2R)-3-cyclopentyl-2-(hydroxymethyl)propanoic acid as a clear, colorless oil (18.5 g, >100%). LCMS: (M+H)+: not detected. 1H NMR (400 MHz, CDCl3): δ 7.3 (br s, 1H), 3.79 (d, J=5.83 Hz, 2H), 2.64-2.71 (m, 1H), 1.45-1.87 (m, 9H), 1.05-0.14 (m, 2H).

1. temperatureThe reaction was warmed to room temperature
2. customThe THF was removed by rotary evaporation
3. washThe aqueous residue was washed with dichloromethane (3×100 mL)
4. extractionwas extracted with ethyl acetate (4×100 mL)
5. dry with materialThe organic extracts were dried (MgSO4)
6. customwere evaporated

ORD record

ord-6d97f3f67299422b8cc30a0572ea5fb6

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893056B2