Trimethylsilane → 5-Benzylhexahydropyrrolo[3,4-c]pyrrole-1-one

HRID 490474Notes

Reaction equation

HRID 490474 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[CH:13]([OH:17])[NH:14][C:15](=O)[CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[SiH](C)C>ClCCl.FC(F)(F)C(O)=O>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH2:15][NH:14][C:13](=[O:17])[CH:11]2[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 70435TrimethylsilaneHCID 671476155-Benzyl-3-hydroxyhexahydropyrrolo[3,4-c]pyrrol-1-one

Product 1

HCID 671476375-Benzylhexahydropyrrolo[3,4-c]pyrrole-1-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
3 °C

Procedure

5-Benzyl-3-hydroxyhexahydropyrrolo[3,4-c]pyrrole-1-one, (7 g; 30 mmol) in suspension in dichloromethane (50 ml) is placed in a 1000 ml three-necked flask and is then cooled in an ice bath. Trimethylsilane (7.1 g; 60 mmol) is run in slowly at 3° C. The reaction mixture is homogeneous and is left to react at 25° C. for 10 minutes, and is then cooled to 3° C. in order to run in trifluoro-acetic acid (50 ml). The reaction mixture is agitated at 20° C. for 16 hours and then evaporated under reduced pressure. The residue is taken up in a mixture of ethyl acetate (100 ml) and 4 N aqueous sodium peroxide (50 ml), separated by settling out and washed with water (100 ml). After drying over magnesium sulfate and evaporation under reduced pressure, a yellow-colored oil is isolated, which is purified by chromatography on silica gel (silica: 40-63 μm eluent: 90/10 ethyl acetate/methanol). The fractions containing the expected compound are combined and then evaporated under reduced pressure, giving 5-benzylhexahydropyrrolo[3,4-c]pyrrole-1-one, (7.2 g) which is used directly in the following step.

Workup

  1. temperatureis then cooled in an ice bath
  2. customslowly at 3° C
  3. waitis left
  4. customto react at 25° C. for 10 minutes
  5. customevaporated under reduced pressure
  6. additionThe residue is taken up in a mixture of ethyl acetate (100 ml) and 4 N aqueous sodium peroxide (50 ml)
  7. customseparated
  8. washwashed with water (100 ml)
  9. dry with materialAfter drying over magnesium sulfate and evaporation under reduced pressure
  10. customa yellow-colored oil is isolated
  11. customwhich is purified by chromatography on silica gel (silica: 40-63 μm eluent: 90/10 ethyl acetate/methanol)
  12. additionThe fractions containing the expected compound
  13. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-65e607c4c2034e838ce5f3d006c5f267
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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