tert-butyl(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamate → tert-Butyl ((1S,5R,6S)-3-azabicyclo[3.3.0]octan-6-yl)carbamate

HRID 2363563Notes

Reaction equation

HRID 2363563 reaction equation
C([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[CH2:9]1[C@H:10]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C@H:11]2[CH2:12][NH:8]1

Participants

5

Reactant 2

HCID 66590514tert-butyl(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 51723436tert-Butyl ((1S,5R,6S)-3-azabicyclo[3.3.0]octan-6-yl)carbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamate (1.06 g, 3.35 mmol) from Step A and ethanol (20 mL) were added to 20% Pd(OH)2 on carbon, wet (212.0 mg, 1.51 mmol) in a 250 mL stainless steel pressure bottle. The reaction mixture was stirred for 16 hours under 30 psi hydrogen at room temperature. The mixture was filtered through a nylon membrane and the solvent was removed in vacuo to give tert-butyl(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamate: 1H NMR (500 MHz, pyridine-d5) δ ppm 4.02-3.99 (m, 1H), 3.03 (d, J=10.4, 1H), 2.98-2.89 (m, 1H), 2.84 (dd, J=10.1, 6.4, 1H), 2.61-2.50 (m, 3H), 2.06-1.98 (m, 1H), 1.91 (td, J=12.9, 6.7, 1H), 1.63 (dt, J=19.5, 7.6, 1H), 1.53 (s, 9H), 1.29-1.23 (m, 1H); MS (ESI+) m/z 227 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ab844abf0e6246468498d4635b24cd14
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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