8,8-Dimethoxy-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]oct-6-ene → 8,8-Dimethoxy-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octane

HRID 1295497Notes

Reaction equation

HRID 1295497 reaction equation
[CH3:1][O:2][C:3]1([O:20][CH3:21])[CH:8]2[CH:9]=[CH:10][CH:4]1[CH2:5][N:6]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:7]2>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:21][O:20][C:3]1([O:2][CH3:1])[CH:4]2[CH2:10][CH2:9][CH:8]1[CH2:7][N:6]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:5]2

Participants

4

Reactant 1

HCID 694336978,8-Dimethoxy-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]oct-6-ene

Product 1

HCID 694287408,8-Dimethoxy-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

8,8-Dimethoxy-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]oct-6-ene (5.92 g, 20.5 mmol) was dissolved in EtOAc (50 mL) in a 250 mL Parr bottle. To this was added catalytic 20% Pd(OH)2/C (Pearlman's catalyst, 500 mg) and the mixture was shaken under 40 psi of H2 for 4 h or until judged complete by TLC. The reaction was filtered through a Celite pad and concentrated to a yellow oil (4.88 g, 82%). (TLC 5% MeOH/CH2Cl2, (NH3) Rf 0.60); 1H NMR (400 MHz, CDCl3) δ 7.21 (d, J=8.3 Hz, 2H), 6.81 (d, J=8.3 Hz, 2H), 3.76 (s, 3H), 3.43 (s, 2H), 3.21 (s, 3H), 3.15 (s, 3H), 2.48 (dd, J=10.3, 3.3 Hz, 2H), 2.36 (d, J=10.3 Hz, 2H), 2.02 (br s, 2H), 1.65 (m, 4H); GCMS m/z 291 (M)+.

Workup

  1. filtrationThe reaction was filtered through a Celite pad
  2. concentrationconcentrated to a yellow oil (4.88 g, 82%)

Sources & evidence

ORD record
ord-748f4eeec478495c9ecadd31e669acf6
Source dataset
uspto-grants-2007_07
Patent number
US07241887B2

Reaction notes

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