Trifluoroacetic acid → Ethyl 2-{8-azabicyclo[3.2.1]octan-3-ylidene}acetate

HRID 1191498Notes

Reaction equation

HRID 1191498 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([O:19][C:17](=[O:18])[CH:16]=[C:11]1[CH2:10][CH:9]2[NH:8][CH:13]([CH2:14][CH2:15]2)[CH2:12]1)[CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58968477Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 58968325Ethyl 2-{8-azabicyclo[3.2.1]octan-3-ylidene}acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-ethoxycarbonylmethylene-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (12.3 g, 41.8 mmol) in CH2Cl2 was added TFA (10 ml) and the reaction was stirred for 8 h. The solution was concentrated under reduced pressure, diluted with CH2Cl2, and washed first with 2 M NaOH and followed by brine. The water phases were thereafter back-extracted with EtOAc and the combined organic phase was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude title product was used without further purification (7.04 g, 37.9 mmol, 91%).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted with CH2Cl2
  3. washwashed first with 2 M NaOH
  4. extractionThe water phases were thereafter back-extracted with EtOAc
  5. dry with materialthe combined organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude title product was used without further purification (7.04 g, 37.9 mmol, 91%)

Sources & evidence

ORD record
ord-d1118f585cf449beb376087e9e2122da
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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