Hydrochloric Acid → Benzyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 857174Notes

Reaction equation

HRID 857174 reaction equation
[CH2:1]1[CH:5]2[CH2:6][N:7](C(OC(C)(C)C)=O)[CH2:8][CH:4]2[CH2:3][N:2]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].Cl.C([O-])([O-])=O.[K+].[K+].O>C(OCC)(=O)C>[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][N:2]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 218675632-Benzyl 5-(tert-butyl) tetrahydropyrrolo[3,4-C]pyrrole-2,5(1H,3H)-dicarboxylate

Product 1

HCID 21867560Benzyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Benzyl tert-butyl tetrahydropyrrolo[3,4-c]pyrrole-2,5(1H, 3H)-dicarboxylate (40 mmol; from step (a) above) was dissolved in ethyl acetate. Ethyl acetate saturated with HCl (g) (500 mL) was added at 0° C. and stirred while reaching room temperature. The solvent was evaporated and the product was dissolved in CH3CN. K2CO3 (4 eq.) and water (2 mL) were added. The mixture was stirred for 2 h, before being filtered and evaporated to give 8 g (82%) of the subtitle compound which was used without further purification in the next step.

Workup

  1. customwhile reaching room temperature
  2. customThe solvent was evaporated
  3. dissolutionthe product was dissolved in CH3CN
  4. stirringThe mixture was stirred for 2 h
  5. filtrationbefore being filtered
  6. customevaporated

Sources & evidence

ORD record
ord-946780d4b33d459dac26277b2c390ae6
Source dataset
uspto-grants-2006_12
Patent number
US07144914B2

Reaction notes

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