Acetonitrile → 1-[2-(Benzyloxy)phenyl]cyclobutan-1-amine

HRID 1697363Notes

Reaction equation

HRID 1697363 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1(C(N)=O)[CH2:18][CH2:17][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.C(#[N:45])C>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([NH2:45])[CH2:18][CH2:17][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 666896801-(2-(Benzyloxy)phenyl)cyclobutanecarboxamide2×

Product 1

HCID 666900331-[2-(Benzyloxy)phenyl]cyclobutan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 1-(2-(benzyloxy)phenyl)cyclobutanecarboxamide (Example 268b 1.984 g) dissolved in acetonitrile (16 mL) and water (16 mL) under nitrogen was treated with [bis(trifluoroacetoxy)iodo]benzene (4.55 g). The resulting solution was stirred at room temperature for 16 h. The reaction mixture was diluted with water, extracted with diethyl ether. The aqueous layer was separated, basified to pH13 with aqueous 1N NaOH and extracted with ethyl acetate. The combined diethyl ether/ethyl acetate organic extracts were dried (MgSO4), filtered and the solvent was removed in vacuo. The residue was dissolved in dichloromethane and loaded on to an SCX cartridge. The impurities were washed through with ethyl acetate then methanol and discarded. Elution with 7N methanolic ammonia and evaporation in vacuo gave the subtitle product (1.164 g).

Workup

  1. extractionextracted with diethyl ether
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined diethyl ether/ethyl acetate organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. dissolutionThe residue was dissolved in dichloromethane
  8. washThe impurities were washed through with ethyl acetate
  9. washElution
  10. customwith 7N methanolic ammonia and evaporation in vacuo

Sources & evidence

ORD record
ord-779d8e2891fa41559291a477bfe2eec5
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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