Potassium tert-butoxide → (4aS,7aR)-Hexahydro-cyclopenta[d][1,3]oxazin-2-one

Temperature

60 °C

To a solution of ((1R,2S)-2-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester (1.6 g, 7.43 mmol) in THF (40 ml) was added potassium tert-butoxide (3.34 g, 29.7 mmol, 4.0 equiv.) at room temperature. After stirring for 1 h at 60° C. the reaction was allowed to warm up to room temperature and after workup with Ethyl acetate/water, drying and concentration in vacuo, the crude material mixture was adsorbed on silica and chromatographed over a prepacked silica column (50 g, 50% to 100% EtOAc in Heptane gradient) to yield 950 mg (91%) of the title compound as a white solid, which was directly used in the next step.

1. temperatureto warm up to room temperature
2. dry with materialafter workup with Ethyl acetate/water, drying
3. concentrationconcentration in vacuo
4. customchromatographed over a prepacked silica column (50 g, 50% to 100% EtOAc in Heptane gradient)

ORD record

ord-c3e7989562804a96ac19cb96d398473f

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221802B2