HCID 22869409, compound → HCID 22869407, compound

HRID 235150Notes

Reaction equation

HRID 235150 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[CH2:19][C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.C(O)(=O)C.[OH-].[OH-].[Pd+2]>[NH2:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[CH2:19][C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 22869409HCID 22869409, compound

Product 1

HCID 22869407HCID 22869407, compoundYield 84.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalyst2×HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 7-dibenzylamino-1-(1-t-butoxycarbonyl-pyrrolidin-2-(R)-ylmethyl)-naphthalene (0.68 g, 1.34 mmol) and 20% palladium hydroxide on carbon (0.25 g) in ethanol (20 mL) and acetic acid (20 mL) was hydrogenated at 50 psi for 8 hours. Additional 20% palladium hydroxide on carbon (0.25 g) was added and hydrogenation was continued overnight. The catalyst (0.3 g) was added a third time and hydrogenation was continued 24 hours more. The reaction was filtered through celite and the pad was washed with ethanol. The filtrate was concentrated and the residue was taken up in ether. This organic phase was extracted with saturated aqueous sodium bicarbonate, water and brine, then it was dried and concentrated to give 0.368 g (84%) of the title compound as a tan foam. A sample recrystallized from ether/hexane as a light tan solid had mp 157°-158.5° C. Analysis calculated for C20H26N2O2 : C, 73.59; H, 8.03; N, 8.58. Found: C, 73.47; H, 7.93; N, 8.37.

Workup

  1. waithydrogenation was continued overnight
  2. waitwas continued 24 hours
  3. filtrationThe reaction was filtered through celite
  4. washthe pad was washed with ethanol
  5. concentrationThe filtrate was concentrated
  6. extractionThis organic phase was extracted with saturated aqueous sodium bicarbonate, water and brine
  7. customit was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d6030c7637c84093b4f2d24b3955163c
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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