Sodium Azide → HCID 18318096, compound

HRID 1795166Notes

Reaction equation

HRID 1795166 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)([CH2:14]OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)([CH2:14][N:26]=[N+:27]=[N-:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22228407HCID 22228407, compound

Product 1

HCID 18318096HCID 18318096, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-cyclohexyl-4-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester, 4, (2.42 g, 6.73 mmol) in DMF (25 mL) is added sodium azide (1.32 g, 20.2 mmol) and the mixture is heated and stirred at 100° C. over night. The reaction is cooled and then quenched with water. The resulting solution is extracted with EtOAc (30 mL), dried, filtered and concentrated in vacuo to afford the crude product as a brown oil which is purified via chromatography on silica gel eluting with hexane/EtOAc 3:1 to afford the desired product in 76% yield (1.91 g) as a colorless oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureThe reaction is cooled
  3. customquenched with water
  4. extractionThe resulting solution is extracted with EtOAc (30 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford the crude product as a brown oil which
  9. customis purified via chromatography on silica gel eluting with hexane/EtOAc 3:1

Sources & evidence

ORD record
ord-d999d4d8d54b4c5bad045313ae08c4a2
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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