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

HRID 923427Notes

Reaction equation

HRID 923427 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>CO.[OH-].[OH-].[Pd+2].[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 102.8%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product from Example 123A (0.56 g, 1.6 mmol) in MeOH (8.0 mL) was added Pd(OH)2/carbon. The mixture was evacuated and a H2 atmosphere was introduced via a balloon. The mixture was stirred overnight then filtered and the solvent was removed under reduced pressure to provide the title compound (0.42 g, 102% yield).

Workup

  1. customThe mixture was evacuated
  2. additiona H2 atmosphere was introduced via a balloon
  3. filtrationthen filtered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9dc87f1063f2473eb6ade5c814c79c82
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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