Sulfuric Acid → 8-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]oct-2-ene

HRID 238270Notes

Reaction equation

HRID 238270 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(O)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12052TriethylsilaneHCID 130912248-Benzyl-3-phenyl-8-azabicyclo[3.2.1]octan-3-ol

Product 1

HCID 4345538-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]oct-2-ene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

8-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]octan-3-ol (0.1 g, 0.34 mmol) was dissolved in TFA (1 mL) and cooled to 0° C. Concentrated sulphuric acid (0.054 mL) was added and the mixture stirred for 1 hour, then triethylsilane (0.17 mL) was added. After 2 hours the mixture was allowed to warm to room temperature, and then to stand for 60 hours. The mixture was concentrated under vacuum and diluted with a solution of saturated aqueous sodium carbonate. The products were extracted into DCM, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum to give the title compound as a colourless oil. LCMS m/z 276.5 [M+H]+. R.T.=2.94 min (Analytical Method 4).

Workup

  1. waitAfter 2 hours the mixture was allowed
  2. temperatureto warm to room temperature
  3. waitto stand for 60 hours
  4. concentrationThe mixture was concentrated under vacuum
  5. additiondiluted with a solution of saturated aqueous sodium carbonate
  6. extractionThe products were extracted into DCM
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-ae7afc9b95b84ad995eb748f300520d0
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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