(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione → (3S,4S)-(+)-1-Benzyl-3,4-pyrrolidindiol

HRID 456249ノート

反応式

HRID 456249 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[C:18](=O)[C@H:17]([OH:20])[C@@H:16]([OH:21])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:18][C@H:17]([OH:20])[C@@H:16]([OH:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 729946(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dioneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 2734057(3S,4S)-(+)-1-Benzyl-3,4-pyrrolidindiol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of LiAlH4 (18.33 g, 219.2 mmol) in 200 mL THF, (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione (23.1 g, 104.4 mmol) was added and the mixture was refluxed for 12 hours. The mixture was cooled down to room temperature and carefully quenched with 3 mL EtOAc and 3 mL MeOH. Wet silica gel was added to the mixture following by addition of MeOH—CHCl3, 1:1, and the mixture was filtered. The filtrate was evaporated giving the title compound that was used for the next step without additional purification.

後処理

  1. additionwas added
  2. temperaturethe mixture was refluxed for 12 hours
  3. customcarefully quenched with 3 mL EtOAc and 3 mL MeOH
  4. additionWet silica gel was added to the mixture
  5. additionfollowing by addition of MeOH—CHCl3, 1:1
  6. filtrationthe mixture was filtered
  7. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-f3b31692598a4313b096282ffeb15ea9
出典データセット
uspto-grants-2013_07
特許番号
US08497383B2

反応ノート

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