Sodium Azide → HCID 86695688, compound

HRID 335341Notes

Reaction equation

HRID 335341 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[O:14]2)(=O)=O)=CC=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C.O.C(OCC)(=O)C>[N:20]([CH2:12][C@@H:13]1[O:14][C:15]([CH3:19])([CH3:18])[CH2:16][CH2:17]1)=[N+:21]=[N-:22]

Participants

6

Reactant 2

HCID 33557Sodium Azide2×HCID 86695689HCID 86695689, compound

Product 1

HCID 86695688HCID 86695688, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

(R)-(5,5-Dimethyltetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (step 1) (12.8 g, 45.0 mmol) in DMF (50 ml) was treated with sodium azide (3.80 g, 58.5 mmol) at RT overnight then warmed to 70° C. for 3 hrs. Sodium azide (3.80 g, 58.5 mmol) was added and the mixture was warmed to 100° C. for 3 hrs, allowed to cool to RT. The mixture was diluted with water and ethyl acetate. The ethyl acetate layer was washed with 0.5 M lithium chloride in water and the organic layers were dried MgSO4, filtered and evaporated to dryness to afford the title compound;

Workup

  1. temperaturethe mixture was warmed to 100° C. for 3 hrs
  2. temperatureto cool to RT
  3. washThe ethyl acetate layer was washed with 0.5 M lithium chloride in water
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9d5e5a0c55a94062af08a0bee7762d3b
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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