Ammonium Chloride → HCID 57481683, compound

HRID 546453Notes

Reaction equation

HRID 546453 reaction equation
[O:1]1[C@@H:7]2[C@H:2]1[CH2:3][C@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:6]2.[Cl-].[NH4+].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C)C=O>[N:15]([C@@H:2]1[C@@H:7]([OH:1])[CH2:6][CH2:5][C@@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1)=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 57481682HCID 57481682, compound

Product 1

HCID 57481683HCID 57481683, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (13.6 g) was dissolved in N,N-dimethyl-formamide (100 ml), ammonium chloride (6.45 g) and sodium azide (7.8 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 12 hours. The solvent was concentrated to about 1/3, and the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (15.8 g) as a colorless oil.

Workup

  1. concentrationThe solvent was concentrated to about 1/3
  2. additionthe residue was diluted with water and ethyl acetate
  3. stirringto conduct stirring for 3 minutes
  4. washThe resultant organic layer was washed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-ed3079153b1841b4951381840fcc6c3f
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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