Sodium Azide → HCID 178500375, compound

HRID 499714Notes

Reaction equation

HRID 499714 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:22])[C:8]([C@H:11]1[CH2:16][CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13][CH2:12]1)([CH3:10])[CH3:9]>CN(C)C=O.O>[CH3:5][O:6][C:7](=[O:22])[C:8]([C@H:11]1[CH2:12][CH2:13][C@H:14]([N:1]=[N+:2]=[N-:3])[CH2:15][CH2:16]1)([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 178500379HCID 178500379, compound

Product 1

HCID 178500375HCID 178500375, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (0.761 g) is added to a solution of 0.898 g of cis-2-(4-methanesulfonyloxy-cyclohexyl)-2-methyl-propionic acid methyl ester in 7 ml of N,N-dimethylformamide. The reaction mixture is warmed to 100° C. for 16 hours. The mixture is cooled to room temperature, diluted with 20 ml of water and extracted with tert-butyl methyl ether (3×30 ml). The combined organic phases are washed with brine (20 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is identified from the residue by means of flash chromatography (SiO2 60 F) based on its Rf value.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with tert-butyl methyl ether (3×30 ml)
  3. washThe combined organic phases are washed with brine (20 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c8b9235aa7a64d2d9df5fc39c0400c47
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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