tert-Butanol → (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane

A solution of AD-mix-α (30 g) in a mixture of t-butanol (600 ml) and water (600 ml) was stirred for 1 hour, and then methanesulfonamide (9.3 g) and 1-(4,5-diphenyloxazol-2-yl)-1-cyclohexene added to the solution at room temperature. After stirring the mixture for 20 hours at the same temperature, sodium sulfite (60 g) was added, and the mixture was stirred for 30 minutes. The mixture was partitioned between EtOAc and water. The organic layer was washed with 1N-hydrochloric acid solution, saturated sodium hydrogencarbonate and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane (30 g).

1. additionwas added
2. stirringthe mixture was stirred for 30 minutes
3. customThe mixture was partitioned between EtOAc and water
4. washThe organic layer was washed with 1N-hydrochloric acid solution, saturated sodium hydrogencarbonate and brine
5. dry with materialdried over magnesium sulfate
6. customevaporated in vacuo
7. customThe residue was purified by chromatography on silica gel

ORDレコード

ord-fd34953ddac64e40aeb8c91e3cad3453

出典データセット

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06437146B1