1-Benzyl-3,4-dihydroxypyrrolidine-2,5-dione → 90365-74-5

HRID 456249Notes

Reaction equation

HRID 456249 reaction equation
[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

Participants

4

Reactant 2

HCID 7299461-Benzyl-3,4-dihydroxypyrrolidine-2,5-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 273405790365-74-5

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f3b31692598a4313b096282ffeb15ea9
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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