Sodium Azide → HCID 14415573, compound

HRID 1782760Notes

Reaction equation

HRID 1782760 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C@H:5]12[CH2:13][C@H:9]([O:10][C:11]1=[O:12])[CH:8]=[CH:7][CH2:6]2>O.C1COCC1>[N:1]([C@H:9]1[CH:8]=[CH:7][CH2:6][C@H:5]([C:11]([OH:12])=[O:10])[CH2:13]1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 10953490HCID 10953490, compound

Product 1

HCID 14415573HCID 14415573, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.6 g of sodium azide in 70 ml of water is added to a solution of 18.4 g of racemic cis-6-oxabicyclo[3.2.1]oct-3-en-7-one in 175 ml of THF. The reaction mixture is then heated to reflux for 15 hours. The THF is subsequently stripped off in a rotary evaporator at a bath temperature of 30° C. The remaining aqueous phase is mixed with 165 ml of 2 molar sodium hydroxide solution and extracted twice with 110 ml of toluene each time and once with diethyl ether. The aqueous phase is then acidified with concentrated hydrochloric acid at about 10° C. The product is extracted with dichloromethane. The organic extract is dried over anhydrous sodium sulphate, filtered and concentrated. 19.7 g of an oil, which becomes solid under storage in a refrigerator, are obtained. Assignment of the product to the trans isomer results from the experience that reactions of this type take place with inversion of the stereochemistry at the reaction site.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureto reflux for 15 hours
  3. customThe THF is subsequently stripped off in a rotary evaporator at a bath temperature of 30° C
  4. additionThe remaining aqueous phase is mixed with 165 ml of 2 molar sodium hydroxide solution
  5. extractionextracted twice with 110 ml of toluene each time
  6. customis then acidified with concentrated hydrochloric acid at about 10° C
  7. extractionThe product is extracted with dichloromethane
  8. extractionThe organic extract
  9. dry with materialis dried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customare obtained
  13. customAssignment of the product to the trans isomer results from the experience that reactions of this type

Sources & evidence

ORD record
ord-b2bdd75d71cb48f38d771cefe821ffc4
Source dataset
uspto-grants-2009_03
Patent number
US07498460B2

Reaction notes

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