Ammonium Chloride → (3S,4R)-4-Azidotetrahydro-3-furanol

HRID 413228Notes

Reaction equation

HRID 413228 reaction equation
[O:1]1[CH:6]2[CH:2]1[CH2:3][O:4][CH2:5]2.[N-:7]=[N+:8]=[N-:9].[Na+].[Cl-].[NH4+]>CO>[N:7]([C@@H:6]1[CH2:5][O:4][CH2:3][C@H:2]1[OH:1])=[N+:8]=[N-:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 675113,6-Dioxabicyclo[3.1.0]hexane

Product 1

HCID 89315345(3S,4R)-4-Azidotetrahydro-3-furanolYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

3,4-Epoxytetrahydrofuran (9 g, 105 mmol) was added to a stirred solution of sodium azide (27 g, 415 mmol) and ammonium chloride (9 g, 159 mmol) in aqueous methanol (95%, 200 ml). The reaction was heated to 75° C. and stirred for 20 hours. The reaction was cooled, filtered and evaporated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate, dried and evaporated under reduced pressure to afford the title compound as a colourless oil, 10 g, 74% yield.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. customdried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b6439e533ef14e91a671cf9c1bec9168
Source dataset
uspto-grants-2003_05
Patent number
US06566373B2

Reaction notes

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