Sodium Hydroxide → 5-Benzyl-3-hydroxyhexahydropyrrolo[3,4-c]pyrrol-1-one

HRID 490475

Reaction equation

HRID 490475 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[C:13](=[O:17])[NH:14][C:15](=[O:16])[CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(=O)[C@@H]2CNC[C@@H]2C(=O)N1.[H-].[H-].[H-].[H-].[Al+3].[Li+].[OH-].[Na+]>O1CCCC1.O>[CH2:1]([N:8]1[CH2:12][CH:11]2[CH:13]([OH:17])[NH:14][C:15](=[O:16])[CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 45649025-Benzyl-octahydropyrrolo(3,4-c)pyrrole-1,3-dioneHCID 21226445Aluminium lithium hydrideHCID 51072220rac-(3aR,6aS)-octahydropyrrolo[3,4-c]pyrrole-1,3-dione

Product 1

HCID 671476155-Benzyl-3-hydroxyhexahydropyrrolo[3,4-c]pyrrol-1-oneYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3 °C

Procedure

A solution of 5-benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione, (12.7 g; 55 mmol) {preparation described for the preparation of cis-perhydropyrrolo[3,4-c]pyrrole-1,3-dione (b)} is added to a suspension of lithium aluminum tetrahydride (2 g; 55 mmol) in tetrahydrofuran, cooled to 3° C. in an ice bath, in a 500 ml three-necked flask. The reaction mixture is agitated at this temperature for 25 minutes and then water (2 ml), 4 N aqueous sodium hydroxide (2 ml) and water (6 ml) are successively added. The solid thus formed is removed by filtration; the filtrate is dried over magnesium sulfate and then evaporated under reduced pressure, resulting in a white solid which is triturated in diisopropyl ether (50 ml). The solid formed is filtered off, washed with diisopropyl ether (25 ml), and then dried under reduced pressure at constant weight. 5-Benzyl-3-hydroxyhexahydropyrrolo[3,4-c]pyrrol-1-one (7 g; 55%) is isolated, the characteristics of which are as follows:

Workup

  1. customThe solid thus formed
  2. customis removed by filtration
  3. dry with materialthe filtrate is dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customresulting in a white solid which
  6. customis triturated in diisopropyl ether (50 ml)
  7. customThe solid formed
  8. filtrationis filtered off
  9. washwashed with diisopropyl ether (25 ml)
  10. customdried under reduced pressure at constant weight

Sources & evidence

ORD record
ord-f23182a2566c4bac93666d927a3a49ff
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Linked notes

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