HCID 18434422, compound → HCID 15388802, compound

HRID 741678Notes

Reaction equation

HRID 741678 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:17][CH:18]=1)=[C:8]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:7][CH2:6]2>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]([C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)=[N:17][CH:18]=1)[C@@H:8]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 18434422HCID 18434422, compound

Product 1

HCID 15388802HCID 15388802, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

Pd(OH)2 (20% 77 mg) was flame dried under vacuum and was added to a solution of 5-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)-2-(2-pyrrolidin-1-ylethoxy)pyridine (286.4 mg, 0.6714 mmol) in acetic acid (50 mL). The mixture was hydrogenated on a Parr shaker at 50 psi and at 50° C. for 16 h. The catalyst was filtered off with the aid of celite and the acetic acid was removed in vacuo. 1H NMR indicated that the reaction was incomplete and the residue was resubjected to the reaction conditions (50 psi and 60° C.) for an additional 6 h. The catalyst was removed via filtration through celite and the solvent was removed in vacuo. Radial chromatography (solvent gradient, CH2Cl2 to 10% MeOH in CH2Cl2) provided the desired material (207 mg, 72%). 1H NMR (250 MHz, CDCl3): δ 7.19 (m, 4H), 6.84 (m, 3H), 6.75 (d, J=2.4 Hz, 1H), 6.68 (dd, J=2.4, 8.4 Hz, 1H), 6.59 (dd, J=2.4, 8.4 Hz, 1H), 6.40 (d, J=8.4 Hz, 1H), 4.35 (t, J=5.7 Hz, 2H), 4.21 (d, J=4.8 Hz, 1H), 3.82 (s, 3H), 3.38 (m, 1H), 3.06 (m, 2H), 2.90 (t, J=5.7 H 2.69 (m, 4H), 2.11 (m, 2H), 1.84 (m, 4H).

Workup

  1. customdried under vacuum
  2. filtrationThe catalyst was filtered off with the aid of celite
  3. customthe acetic acid was removed in vacuo
  4. customthe residue was resubjected to the reaction conditions (50 psi and 60° C.) for an additional 6 h
  5. customThe catalyst was removed via filtration through celite
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c921c0f313f34a36a56d84b29ab5cfbc
Source dataset
uspto-grants-1996_09
Patent number
US05552412

Reaction notes

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