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

HRID 275599

反応式

HRID 275599 の反応式
[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

参加物

6

反応物 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 67807920Benzyl rac-alpha-[[[1-methyl-1-(3-pyrrolin-1-ylcarbonyl)ethyl]sulfonyl]methyl]hydrocinnamate

生成物 1

HCID 54545256benzyl (RS)-alpha-[[[1-[[(3RS,4RS)-3,4-dihydroxy-1-pyrrolidinyl]carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate収率 74.7%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-8e9c9d0643dc480681abc8cc10c88bc9
出典データセット
uspto-grants-1995_02
特許番号
US05393875

関連ノート

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