Acetic Acid → Tert-butyl 5-amino-octahydrocyclopenta[c]pyrrole-2-carboxylate

HRID 1056632Notes

Reaction equation

HRID 1056632 reaction equation
C([NH:8][CH:9]1[CH2:23][CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]2[CH2:10]1)C1C=CC=CC=1.CC(O)=O>CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]1[CH2:23][CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:15][CH:11]2[CH2:10]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69225608tert-butyl 5-(benzylamino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 59011518Tert-butyl 5-amino-octahydrocyclopenta[c]pyrrole-2-carboxylateYield 86.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 5-(benzylamino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (6.50 g, 20.5 mmol) and AcOH (1.23 g, 20.5 mmol) in MeOH (150 mL) was added Pd(OH)2/C (10% wt, 1.00 g), and the suspension was stirred at 40° C. under H2 atmosphere overnight. The mixture was filtered through a pad of Celite and then concentrated in vacuo. The residue was dissolved in saturated NaHCO3 solution (70 mL) and extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL×3), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo to give the title compound as a yellow solid (4.00 g, 86.2%).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in saturated NaHCO3 solution (70 mL)
  4. extractionextracted with DCM (100 mL×3)
  5. washThe combined organic phases were washed with brine (100 mL×3)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3f981b837af41ad819a6a72697782cc
Source dataset
uspto-grants-2016_07
Patent number
US09399637B2

Reaction notes

Loading…