Hydrogen Bromide → 1,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

HRID 1534809Notes

Reaction equation

HRID 1534809 reaction equation
C1(O)C=CC=CC=1.C1(C)C=CC(S([N:17]2[CH2:24][C:23]3[CH2:22][N:21](S(C4C=CC(C)=CC=4)(=O)=O)[CH2:20][C:19]=3[CH2:18]2)(=O)=O)=CC=1.[BrH:36]>>[BrH:36].[BrH:36].[C:19]12[CH2:20][NH:21][CH2:22][C:23]=1[CH2:24][NH:17][CH2:18]2

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 151922522,5-Ditosyl-1,2,3,4,5,6-hexahydropyrrolo[3,4-c]pyrrole

Product 1

HCID 232828491,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

Procedure

60 ml of 48% hydrobromic acid and 7 g of phenol were added to 10.8 g 3,7-bis-p-toluenesulfonyl-3,7-diazabicyclo [3.3.0]oct-1(5)-ene, prepared in Preparation 1. The mixture was refluxed for 4 hours and cooled to room temperature. The aqueous phase was separated by adding 100 ml of chloroform and 50 ml of water. The aqueous phase was washed with chloroform (100 ml×4) and decolorized with active carbon. The aqueous phase was concentrated under vacuum and the remained solid was washed with 1:1 methanol-ethyl ether solvent. 5 g of the title compound was obtained as white solid (yield 71%).

Workup

  1. customprepared in Preparation 1
  2. temperatureThe mixture was refluxed for 4 hours
  3. customThe aqueous phase was separated
  4. additionby adding 100 ml of chloroform and 50 ml of water
  5. washThe aqueous phase was washed with chloroform (100 ml×4)
  6. concentrationThe aqueous phase was concentrated under vacuum
  7. washthe remained solid was washed with 1:1 methanol-ethyl ether solvent

Sources & evidence

ORD record
ord-9979fa4531894658a16206b26a561fe7
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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