Sodium Azide → (3R,3aR,6S,6aR)-6-azido-hexahydro-furo[3,2-b]furan-3-ol

HRID 416121Notes

Reaction equation

HRID 416121 reaction equation
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@@H:9](OS(C3C=CC(C)=CC=3)(=O)=O)[C@H:5]2[O:4][CH2:3]1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([C@@H:9]1[C@H:5]2[O:4][CH2:3][C@@H:2]([OH:1])[C@H:6]2[O:7][CH2:8]1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 13014014(3R,3aS,6R,6aR)-6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Product 1

HCID 51345858(3R,3aR,6S,6aR)-6-azido-hexahydro-furo[3,2-b]furan-3-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.5 g of toluene-4-sulfonic acid (3R,3aS,6R,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester in 30 ml of DMF is heated with 0.8 g of sodium azide under reflux for 2 hours, solvent is distilled off and the distillation residue obtained is dissolved in EtAc and extracted with H2O. The organic phase obtained is dried and solvent is evaporated. (3R,3aR,6S,6aR)-6-azido-hexahydro-furo[3,2-b]furan-3-ol is obtained.

Workup

  1. temperatureunder reflux for 2 hours
  2. distillationsolvent is distilled off
  3. customthe distillation residue obtained
  4. dissolutionis dissolved in EtAc
  5. extractionextracted with H2O
  6. customThe organic phase obtained
  7. customis dried
  8. customsolvent is evaporated

Sources & evidence

ORD record
ord-0d499233193a460f93492120885ad6d3
Source dataset
uspto-grants-2012_01
Patent number
US08088823B2

Reaction notes

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