Triphenylphosphine → HCID 66728699, compound

HRID 518773Notes

Reaction equation

HRID 518773 reaction equation
[N:1]([CH:4]1[CH2:7][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)([C:8]#[N:9])[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O.Cl.CCOC(C)=O>[NH2:1][CH:4]1[CH2:7][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)([C:8]#[N:9])[CH2:5]1

Participants

7

Reactant 2

HCID 11776TriphenylphosphineHCID 86692830HCID 86692830, compound

Product 1

HCID 66728699HCID 66728699, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-azido-1-(pyridin-2-yl)cyclobutanecarbonitrile (3.375 g, 16.94 mmol) in THF (30 mL) and water (8 mL) was added triphenylphosphine (5.33 g, 20.33 mmol) with cooling and stirring in an ice-water bath. The mixture was stirred at RT overnight. The reaction was diluted with 1N aqueous HCl and EtOAc. The acidic aqueous layer was separated and retained. The organic layer was washed with water, and then the combined aqueous layers were washed with EtOAc and basified by addition of 6 N aq NaOH. The product amine was extracted with EtOAc. The organic phase was concentrated to afford the title compound as a colorless oil and a 3:1 mixture of geometrical isomers, which was dried under vacuum and used without further purification.

Workup

  1. temperaturewith cooling
  2. stirringThe mixture was stirred at RT overnight
  3. customThe acidic aqueous layer was separated
  4. washThe organic layer was washed with water
  5. washthe combined aqueous layers were washed with EtOAc
  6. additionbasified by addition of 6 N aq NaOH
  7. extractionThe product amine was extracted with EtOAc
  8. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-bcf84690d5c34e489d362fa4fe76e298
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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