HCID 15479426, compound → HCID 15479427, compound

HRID 1954075Notes

Reaction equation

HRID 1954075 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH:3]([C:8](=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=1)[NH:2]2>C(OCC)(=O)C.[Pd]>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:8](=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=1)[NH:2]2

Participants

4

Reactant 1

HCID 15479426HCID 15479426, compound

Product 1

HCID 15479427HCID 15479427, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 85 mg of 1-(2-Aza-bicyclo[2.2.1]hept-5-en-3-yl)-5-(3,4,5-trimethoxy-phenyl)-pentan-1-one and 50 mg of 10% Pd/C in 10 ml of ethyl acetate was hydrogenated at 50 psi for 6 hours. The reaction mixture was filtered and the solvent evaporated to yield 85 mg of 1-(2-Aza-bicyclo[2.2.1]hept-3-yl)-5-(3,4,5-trimethoxy-phenyl)-pentan-1-one as a mixture of exo and endo isomers. 1H NMR: (CDCl3) δ 6.40 (s, 2 H), 3.8 (s, 6 H), 3,75 (s, 3 H), 3.0-4.2 (m, 2 H), 2.5 (m, 5 H), 1.6 (m, 4 H), 1.4 (m, 1 H), 1.2 (m, 1 H). Mass spectrum m/e=348.2 (P+1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-be22b256692646f286fad7e0dc9375ab
Source dataset
uspto-grants-2000_09
Patent number
US06121280

Reaction notes

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