HCID 69593396, compound → HCID 69593412, compound

HRID 1793643Notes

Reaction equation

HRID 1793643 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.CCOC(C)=O.O=[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[CH2:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 69593396HCID 69593396, compound

Product 1

HCID 69593412HCID 69593412, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3,4-Dichloro-benzylidene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (1.0 g, 2.7 mmol) in 10 mL of EtOH and 10 mL of EtOAc was stirred with 25 mg of PtO2 under 1 atm of H2 at rt for 3 h. It was then filtered through a celite bed and the filtrate was concentrated. The residue was purified on a silica gel column to give 0.84 g of 3-(3,4-dichloro-benzyl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (M++1: 370).

Workup

  1. filtrationIt was then filtered through a celite bed
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-ebee6e095942447a958113ac2ece4f20
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

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