Sodium Azide → HCID 86692830, compound

HRID 518772Notes

Reaction equation

HRID 518772 reaction equation
CS(O[CH:6]1[CH2:9][C:8]([C:16]#[N:17])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:7]1)(=O)=O.[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C.CCOC(C)=O.O>[N:18]([CH:6]1[CH2:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)([C:16]#[N:17])[CH2:7]1)=[N+:19]=[N-:20]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 86692829HCID 86692829, compound

Product 1

HCID 86692830HCID 86692830, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-cyano-3-(pyridin-2-yl)cyclobutyl methanesulfonate (4.008 g, 15.89 mmol) in dry DMF (20 mL) was added sodium azide (2.066 g, 31.8 mmol), and the mixture was stirred in an oil bath at 90° C. for 48 hours under a N2 atmosphere. The reaction was diluted with EtOAc and water, and the layers were separated. The organic layer was washed with water and concentrated under vacuum. The residue was chromatographed on silica gel, eluting with 40% EtOAc/hexane to afford the title compound, a 3:1 mixture of geometrical isomers, as a colourless oil m/z 200 MH+.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under vacuum
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 40% EtOAc/hexane

Sources & evidence

ORD record
ord-17da7386d40e47668f4558a31ca4ca49
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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