3-Benzyl-8,8-dimethoxy-3-aza-bicyclo[3.2.1]oct-6-ene → HCID 43810849, compound

HRID 1295493Notes

Reaction equation

HRID 1295493 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[C:15]([O:18][CH3:19])([O:16][CH3:17])[CH:10]([CH:11]=[CH:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH2:1]([N:8]1[CH2:14][CH:13]2[C:15]([O:18][CH3:19])([O:16][CH3:17])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 589077523-Benzyl-8,8-dimethoxy-3-aza-bicyclo[3.2.1]oct-6-ene

Product 1

HCID 43810849HCID 43810849, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Benzyl-8,8-dimethoxy-3-aza-bicyclo[3.2.1]oct-6-ene (51.8 g, 0.2 mol) was dissolved in EtOAc (100 mL) in a 500 mL Parr bottle. To this was added 20% Pd(OH)2/C (Degussa type, 2.60 g) and the mixture was shaken under 45 psi of H2 for 4 h (or judged complete by TLC). The reaction was filtered through a Celite pad, rinsed with EtOAc, and concentrated to a brown liquid (50.4 g, 97%). (TLC 30% EtOAc/hexanes Rf 0.63); 1H NMR (400 MHz, CDCl3) δ 7.33–7.17 (5H), 3.51 (s, 2H), 3.22 (s, 3H), 3.16 (s, 3H), 2.50 (AB dd, J=10.4, 3.7 Hz, 2H), 2.40 (AB d, J=10.4 Hz, 2H), 2.04 (br s, 2H), 1.70–1.64 (m, 4H); APCI MS m/z 262.3 (M+1)+.

Workup

  1. filtrationThe reaction was filtered through a Celite pad
  2. washrinsed with EtOAc
  3. concentrationconcentrated to a brown liquid (50.4 g, 97%)

Sources & evidence

ORD record
ord-de8753d9e9894277b809a76a8c5e35aa
Source dataset
uspto-grants-2007_07
Patent number
US07241887B2

Reaction notes

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