N-Methylmorpholine N-oxide monohydrate → HCID 54545256, compound

HRID 275599

Reaction equation

HRID 275599 reaction equation
[OH2:1].C[N+]1([O-])CC[O:6]CC1.[CH3:10][C:11]([S:20]([CH2:23][CH:24]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])(=[O:22])=[O:21])([C:13]([N:15]1[CH2:19][CH:18]=[CH:17][CH2:16]1)=[O:14])[CH3:12]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:1][CH:17]1[CH:18]([OH:6])[CH2:19][N:15]([C:13]([C:11]([S:20]([CH2:23][CH:24]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])(=[O:21])=[O:22])([CH3:10])[CH3:12])=[O:14])[CH2:16]1

Participants

6

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 67807920HCID 67807920, compound

Product 1

HCID 54545256HCID 54545256, compoundYield 74.7%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-8e9c9d0643dc480681abc8cc10c88bc9
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Linked notes

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