8-Azabicyclo[3.2.1]oct-2-ene, 8-methyl-3-(2-naphthalenyl)- → HCID 18689926, compound

HRID 1871910Notes

Reaction equation

HRID 1871910 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:17][CH:16]2[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]2)[CH:12]=1>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:17][CH:16]2[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1

Participants

3

Reactant 1

HCID 119553718-Azabicyclo[3.2.1]oct-2-ene, 8-methyl-3-(2-naphthalenyl)-

Product 1

HCID 18689926HCID 18689926, compoundYield 1.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.3 gm (5.22 mMol) 3-(naphth-2-yl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene in 25 mL ethanol containing 1.3 gm 10% palladium on carbon was stirred at room temperature under a hydrogen atmosphere maintained by a balloon for 8 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a gradient of dichloromethane containing 2-10% methanol and 30% of dichloromethane saturated with ammonia. Frac-tions containing product were combined and concentrated under reduced pressure to provide 0.020 gm (1.7%) of the title compound as a white solid.

Workup

  1. temperaturemaintained by a balloon for 8 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. washeluting with a gradient of dichloromethane containing 2-10% methanol and 30% of dichloromethane saturated with ammonia
  5. additionFrac-tions containing product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88095fbe43794d88b05ea7ec26c4bec0
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

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