Acetic Acid → Octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrobromide

HRID 60860Notes

Reaction equation

HRID 60860 reaction equation
C([N:4]1[CH2:8][CH:7]2[CH2:9][CH2:10][CH2:11][CH:6]2[C:5]1(C(OCC)=O)[C:12]([O:14]CC)=[O:13])(=O)C.CC(O)=O.[BrH:26]>>[BrH:26].[CH:5]1([C:12]([OH:14])=[O:13])[CH:6]2[CH2:11][CH2:10][CH2:9][CH:7]2[CH2:8][NH:4]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 86587089Diethyl 2-acetylhexahydrocyclopenta[c]pyrrole-1,1(2H)-dicarboxylate

Product 1

HCID 117727800Octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrobromide

Conditions

Temperature
120 °C

Procedure

A solution of the rac-diethyl 2-acetylhexahydrocyclopenta[c]pyrrole-1,1(2H)-dicarboxylate prepared above in 48% aqueous HBr and AcOH (4:1) was heated at 120° C. for 16 h. The reaction mixture was cooled, concentrated in vacuo and lyophilized to yield the title compound. MS (ESI) 156 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03dbab428d564c579c1a7d499dae9b94
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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