HCID 14514526, compound → (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 1431870Notes

Reaction equation

HRID 1431870 reaction equation
[N:1]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:5]([C:6]([O:8]CC2C=CC=CC=2)=[O:7])[CH2:4][C@@H:3]2[CH2:16][CH2:17][CH2:18][C@H:2]12>[Pd].C(O)C>[C:22]([O:21][C:19]([N:1]1[C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][C@@H:3]2[CH2:16][CH2:17][CH2:18][C@H:2]12)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 1

HCID 14514526HCID 14514526, compound

Product 1

HCID 15622962(2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 104.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 250 mL round bottom flask charged with a stir bar and (2S,3aS,6aS)-2-benzyl 1-tert-butyl hexahydrocyclopenta[b]pyrrole-1,2(2H)-dicarboxylate (5.76 g, 16.68 mmol) was added 10% Palladium on carbon (1.77 g). Ethanol was poured over the mixture and the reaction mixture was evacuated and flushed with hydrogen gas three times. The suspension was stirred at room temperature under an atmosphere of hydrogen for 24 hours. Upon completion, the reaction mixture was filtered through celite and concentrated to give (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid (4.45 g, >99%). MS (ESI) m/z 256.21 [M+H]+.

Workup

  1. additionTo a 250 mL round bottom flask charged with a stir bar
  2. customthe reaction mixture was evacuated
  3. customflushed with hydrogen gas three times
  4. filtrationUpon completion, the reaction mixture was filtered through celite and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7848c00488984a388516ebdf4c039fa0
Source dataset
uspto-grants-2015_01
Patent number
US08940718B2

Reaction notes

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