Dimethylformamide → 2-[3-(2-Naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethanol

HRID 987575Notes

Reaction equation

HRID 987575 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[NH:18][CH:13]([CH2:14][CH2:15]2)[CH:12]=1.Br[CH2:20][CH2:21][OH:22].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[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[CH2:12][CH:13]2[N:18]([CH2:20][CH2:21][OH:22])[CH:16]([CH2:15][CH2:14]2)[CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 119560113-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-ene

Product 1

HCID 180091722-[3-(2-Naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethanolYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Naphthalen-2-yl-8-aza-bicyclo[3.2.1]oct-2-ene (1.00 g, 4.25 mmol), 1.05 g (8.40 mmol) 2-bromoethanol, 1.70 g (12.6 mmol) K2CO3 and 57 mL of DMF are stirred at 80 C for 12 h. The reaction mixture is poured into 300 mL of cold H2O and extracted with 3×50 mL of EtOAc. The combined organics are washed with 3×100 mL of H2O, 1×100 mL of brine, dried over MgSO4, filtered, and the volatiles are evaporated to give 1.08 g (3.87 mmol, a 91% yield) of the title compound as a white solid. mp: 113-114° C.; MS (ES) m/z 280 (MH)+.

Workup

  1. extractionextracted with 3×50 mL of EtOAc
  2. washThe combined organics are washed with 3×100 mL of H2O, 1×100 mL of brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe volatiles are evaporated
  6. customto give 1.08 g (3.87 mmol

Sources & evidence

ORD record
ord-bbe2f7a2f2d24fd187108936f3340705
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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