HCID 12621144, compound → HCID 12621142, compound

HRID 372091Notes

Reaction equation

HRID 372091 reaction equation
[CH3:1][N:2]1[CH2:6][C:5]23[CH2:16][CH:9]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:4]2=[CH:3]1)[C:8]1[CH:17]=[CH:18][CH:19]=[CH:20][C:7]3=1.[H][H]>[Pd].C(O)(=O)C>[CH3:1][N:2]1[CH2:6][C:5]23[CH2:16][CH:9]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[CH:4]2[CH2:3]1)[C:8]1[CH:17]=[CH:18][CH:19]=[CH:20][C:7]3=1

Participants

5

Reactant 2

HCID 12621144HCID 12621144, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12621142HCID 12621142, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 13.6 g of 2-methyl-2,3-dihydro-8H-3a, 8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole, 100 ml of acetic acid and 2 g of 10% palladium-on-charcoal catalyst is shaken under 40 psi hydrogen pressure at room temperature until the pressure remains constant. The filtered mixture is concentrated, the residue is made basic and extracted several times with methylene chloride. Removal of the solvent from the dried extracts gives 13.7 g of 2-methyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4;6,7]-cyclohepta[1,2-c]pyrrole (1c) identical by nmr spectroscopy with the product obtained in Example 1.

Workup

  1. concentrationThe filtered mixture is concentrated
  2. extractionextracted several times with methylene chloride
  3. customRemoval of the solvent from the dried extracts

Sources & evidence

ORD record
ord-3fe1ac4a73f743608e93e72e58a30bad
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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