Trifluoroacetic acid → 2-Acetyl-3-methyl-8-azabicyclo[3.2.1]oct-2-ene

HRID 483783Notes

Reaction equation

HRID 483783 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:11]1[CH:12]2[N:19](C(OC(C)(C)C)=O)[CH:15]([CH2:16][C:17]=1[CH3:18])[CH2:14][CH2:13]2)(=[O:10])[CH3:9]>>[C:8]([C:11]1[CH:12]2[NH:19][CH:15]([CH2:16][C:17]=1[CH3:18])[CH2:14][CH2:13]2)(=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 197513552-Acetyl-3-methyl-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]oct-2-en

Product 1

HCID 197513562-Acetyl-3-methyl-8-azabicyclo[3.2.1]oct-2-ene

Procedure

A solution of trifluoroacetic acid (18.8 mmol, 2.14 ml) and 2-acetyl-3-methyl-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]oct-2-en (0.49 g, 1.88 mmol) was stirred at room temperature for about 0.5 hour. The solution was concentrated under reduced pressure. Hexane was added to the resulting residue, the resulting solution was concentrated under reduced pressure, and the process was repeated a second time to remove any residual trifluoroacetic acid. A concentrated solution of sodium carbonate was added to the residue to form a basic solution. The solution was extracted with methylene chloride, dried using sodium sulfate and purified by bulb-to-bulb distillation (80° C. (1.0 mmHg)) to give 2-acetyl-3-methyl-8-azabicyclo[3.2.1]oct-2-ene.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionHexane was added to the resulting residue
  3. concentrationthe resulting solution was concentrated under reduced pressure
  4. customto remove any residual trifluoroacetic acid
  5. additionA concentrated solution of sodium carbonate was added to the residue
  6. customto form a basic solution
  7. extractionThe solution was extracted with methylene chloride
  8. customdried
  9. distillationpurified by bulb-to-bulb distillation (80° C. (1.0 mmHg))

Sources & evidence

ORD record
ord-7f78b16bc23c4a879ebd1c777b4e757b
Source dataset
uspto-grants-1993_07
Patent number
US05227385

Reaction notes

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