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

HRID 1975820Notes

Reaction equation

HRID 1975820 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, 2.13 mL) and 2-Acetyl-3-methyl-8-(tert-butyloxycarbonyl)-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 three times under reduced pressure after the addition of hexane to remove excess 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 three times under reduced pressure
  2. additionafter the addition of hexane
  3. customto remove excess trifluoroacetic acid
  4. additionA concentrated solution of sodium carbonate was added to the residue
  5. customto form a basic solution
  6. extractionThe solution was extracted with methylene chloride
  7. customdried
  8. distillationpurified by bulb-to-bulb distillation (80° C. (1.0 mmHg))

Sources & evidence

ORD record
ord-89dd037da98b4ca6929c19bd8300800a
Source dataset
uspto-grants-1994_02
Patent number
US05288872

Reaction notes

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