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

HRID 456249노트

반응식

HRID 456249 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f3b31692598a4313b096282ffeb15ea9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497383B2

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