Sodium Azide → HCID 131727661, compound

HRID 1016147Notes

Reaction equation

HRID 1016147 reaction equation
[CH3:1][NH:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([C:11]([O:13][CH3:14])=[O:12])[CH2:6]1)=O.[N-:15]=[N+:16]=[N-:17].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(#N)C.CCOC(C)=O>[CH3:1][N:2]1[C:3]([C@@H:5]2[CH2:10][CH2:9][CH2:8][C@H:7]([C:11]([O:13][CH3:14])=[O:12])[CH2:6]2)=[N:17][N:16]=[N:15]1

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 131727662HCID 131727662, compound

Product 1

HCID 131727661HCID 131727661, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(±)-cis-Methyl 3-(methylcarbamoyl)cyclohexanecarboxylate (460 mg, 2.309 mmol) was dissolved in Acetonitrile (5 mL) at 25° C. under nitrogen with stirring, then sodium azide (150 mg, 2.309 mmol) was added. Cooled to 0° C. then added trifluoromethanesulfonic anhydride (0.390 mL, 2.309 mmol) dropwise over 2 minutes. The reaction was a colorless solution. Stirred for 20 hours then added sat'd sodium bicarbonate and stirred for 15 minutes, then added a little EtOAc and concentrated in vacuo the acetonitrile. Added more EtOAc and separated the layers. The EtOAc layer was rinsed again with sat'd sodium bicarbonate then 1 time with brine. The EtOAc layer was dried over sodium sulfate and stripped to give of a colorless oil. Obtained (±)-cis-methyl 3-(1-methyl-1H-tetrazol-5-yl)cyclohexanecarboxylate (350 mg, 1.561 mmol, 68% yield) as a colorless oil for product. MS found: (M+H)+=225.00.

Workup

  1. stirringStirred for 20 hours
  2. stirringstirred for 15 minutes
  3. concentrationconcentrated in vacuo the acetonitrile
  4. additionAdded more EtOAc
  5. customseparated the layers
  6. washThe EtOAc layer was rinsed again with sat'd sodium bicarbonate
  7. dry with materialThe EtOAc layer was dried over sodium sulfate
  8. customto give of a colorless oil

Sources & evidence

ORD record
ord-88d49735d8b24fdd93b0e27a4398f942
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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