HCID 66996649, compound → (3AR,4R,6aS)-rel-Octahydro-cyclopenta[c]pyrrol-4-ol

HRID 2402746Notes

Reaction equation

HRID 2402746 reaction equation
C([N:8]1[CH2:12][C@@H:11]2[C@H:13]([OH:16])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C>[CH2:9]1[C@H:10]2[CH2:15][CH2:14][C@@H:13]([OH:16])[C@H:11]2[CH2:12][NH:8]1

Participants

4

Reactant 2

HCID 66996649HCID 66996649, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66997095(3AR,4R,6aS)-rel-Octahydro-cyclopenta[c]pyrrol-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3aR,4R,6aS)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-ol (2.88 g, 13.25 mmol) from Example 28 and ethanol (40 mL) were added to 20% Pd(OH)2—C, wet (0.576 g, 4.10 mmol) in a 250 mL stainless steel pressure bottle and stirred for 2 hours at 30 psi hydrogen gas at 50° C. The mixture was filtered through a nylon membrane, and the solvent was removed in vacuo to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 4.82 (s, 4H), 4.37 (dd, J=10.5, 4.8, 1H), 3.52 (dd, J=10.8, 1.7, 1H), 2.96-2.86 (m, 1H), 2.76 (dd, J=10.8, 6.9, 1H), 2.71 (dd, J=10.8, 1.8, 1H), 2.56-2.45 (m, 2H), 1.89 (td, J=11.7, 5.3, 1H), 1.80 (ddd, J=12.5, 10.3, 6.8, 1H), 1.66-1.58 (m, 1H), 1.50-1.42 (m, 1H); MS (ESI+) m/z 128 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-cb947f119c6a4dfabb35244035d3e94d
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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