Citric Acid → HCID 20741415、化合物

HRID 348396ノート

反応式

HRID 348396 の反応式
[C:1]1([C:7]([C@H:9]2[CH2:13][N:12]([C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=[O:22])[CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[OH:8][CH:7]([C@H:9]1[CH2:13][N:12]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:11](=[O:22])[CH2:10]1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 60123706HCID 60123706、化合物

生成物 1

HCID 20741415HCID 20741415、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To an absolute ethanol (40 ml) solution of 4-(R)-phenylcarbonyl-1-[1-(R)-phenylethyl]-2-pyrrolidone (2.17 g, 7.40 mmol) was added sodium borohydride (280 mg) under ice cooling, followed by stirring at the same temperature for 1 hour. To the reaction solution was added 10% citric acid (50 ml) under ice cooling, and then the ethanol was removed under reduced pressure. The residue was extracted with chloroform (80 ml×2) and, after washing with saturated saline (100 ml), the organic layer was dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography. Elution with eluents of n-hexane/ethyl acetate (1/3) to ethyl acetate (100%) afforded the low polar title compound having low polarity [F1] (892 mg, 41%) and the title compound having high polarity [F2] (1.163 g, 53%) as pale yellow oils.

後処理

  1. customthe ethanol was removed under reduced pressure
  2. extractionThe residue was extracted with chloroform (80 ml×2)
  3. washafter washing with saturated saline (100 ml)
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customAfter removal of the solvent under reduced pressure
  6. washElution with eluents of n-hexane/ethyl acetate (1/3) to ethyl acetate (100%)

出典と根拠

ORDレコード
ord-8c547a751e424075b10ccaf4047bae29
出典データセット
uspto-grants-2007_02
特許番号
US07176313B2

反応ノート

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