Hydrogen Bromide → Octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrobromide

HRID 23883Notes

Reaction equation

HRID 23883 reaction equation
C([N:4]1[CH2:11][CH:10]2[CH:6]([CH2:7][CH2:8][CH2:9]2)[C:5]1(C(OCC)=O)[C:12]([O:14]CC)=[O:13])(=O)C.[BrH:22]>CC(O)=O>[BrH:22].[CH:6]12[CH2:7][CH2:8][CH2:9][CH:10]1[CH2:11][NH:4][CH:5]2[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

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

Product 1

HCID 117727800Octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrobromideYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-acetyl-3-azabicyclo[3.3.0]octane-2,2-dicarboxylic acid, diethyl ester (1.9 g, 6.3 mmol) in aqueous HBr (48%, 10 mL) and HOAc (2 mL) was heated at 120° C. under nitrogen for 18 h. The reaction mixture was cooled, concentrated in vacuo, and the residue was azeotroped with acetonitrile (2×) and Et2O/toluene (1×) to yield 3-azabicyclo[3.3.0]octane-2-carboxylic acid, hydrobromide (1.4 g, 93%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customthe residue was azeotroped with acetonitrile (2×) and Et2O/toluene (1×)

Sources & evidence

ORD record
ord-ab62f2163bee461c9ce1765162d22af7
Source dataset
uspto-grants-2005_02
Patent number
US06855708B2

Reaction notes

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