HCID 18434422, compound → HCID 15388802, compound

HRID 1532781Notes

Reaction equation

HRID 1532781 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): δ7.19 (m, 4 H), 6.84 (m, 3 H), 6.75 (d, J=2.4 Hz, 1 H), 6.68 (dd, J=2.4, 8.4 Hz, 1 H), 6.59 (dd, J=2.4, 8.4 Hz, 1 H), 6.40 (d, J=8.4 Hz, 1 H), 4.35 (t, J=5.7 Hz, 2 H), 4.21 (d, J=4.8 Hz, 1 H), 3.82 (s, 3 H), 3.38 (m, 1 H), 3.06 (m, 2 H), 2.90 (t, J=5.7 Hz, 2 H), 2.69 (m, 4 H), 2.11 (m, 2 H), 1.84 (m, 4 H).

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-f1c8cd865b0d491bb2c1f1a7473aebff
Source dataset
uspto-grants-2001_03
Patent number
US06204286B1

Reaction notes

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