N-Methylmorpholine N-oxide monohydrate → benzyl (RS)-alpha-[[[1-[[(3RS,4RS)-3,4-dihydroxy-1-pyrrolidinyl]carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate

832 mg (6.16mmol) of 4-methylmorpholine 4-oxide monohydrate and 10 ml of an osmium tetroxide solution [1.0 g of osmium tetroxide and 1 ml of tert-butyl hydroperoxide (70% in water) in 199 ml of tert-butanol]were added at room temperature to a solution of 935 mg (2.05 mmol) of benzyl rac-α-[[[1-methyl-1-(3-pyrrolin-1-ylcarbonyl)ethyl]sulfonyl]methyl]hydrocinnamate in 30 ml of acetone and 10 ml of water. The reaction mixture was stirred at room temperature for three days. Subsequently, the solvent was evaporated under reduced pressure, the residue was poured into 80 ml of ice-cold 10% citric acid solution and extracted with 240 ml of ethyl acetate. The organic extracts were washed twice with 80 ml of water each time and the combined aqueous phases were back-extracted twice with 80 ml of ethyl acetate each time. The combined ethyl acetate extracts were dried over magnesium sulphate and evaporated under reduced pressure. For purification, the crude product (1.1 g) was chromatographed on 80 g of silica gel with a 1:4 mixture of toluene and ethyl acetate as the eluent. There were obtained 750 mg of benzyl (RS)-α-[[[1-[[(3RS,4RS)-3,4-dihydroxy-1-pyrrolidinyl]carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate as a colourless oil, MS: 490 (M+H)+.

1. customSubsequently, the solvent was evaporated under reduced pressure
2. additionthe residue was poured into 80 ml of ice-cold 10% citric acid solution
3. extractionextracted with 240 ml of ethyl acetate
4. washThe organic extracts were washed twice with 80 ml of water each time
5. extractionthe combined aqueous phases were back-extracted twice with 80 ml of ethyl acetate each time
6. dry with materialThe combined ethyl acetate extracts were dried over magnesium sulphate
7. customevaporated under reduced pressure
8. customFor purification
9. customthe crude product (1.1 g) was chromatographed on 80 g of silica gel with a 1:4 mixture of toluene and ethyl acetate as the eluent

ORD 기록

ord-8e9c9d0643dc480681abc8cc10c88bc9

출처 데이터셋

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05393875