Sodium Azide → Methyl 4-azido-3-hydroxybutyrate

HRID 362666Notes

Reaction equation

HRID 362666 reaction equation
Cl[CH2:2][CH:3]([OH:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[N-:10]=[N+:11]=[N-:12].[Na+]>CN(C)C1C=CN=CC=1.C(C(C)=O)C(C)C>[N:10]([CH2:2][CH:3]([OH:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[N+:11]=[N-:12]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 3629997Methyl 4-chloro-3-hydroxybutanoate

Product 1

HCID 23630755Methyl 4-azido-3-hydroxybutyrateYield 104.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a mixture of methyl 4-chloro-3-hydroxybutyrate (5 g, 33 mmol), and methyl isobutyl ketone (40 ml) are added sodium azide (2.3 g, 36 mmol) and 4-dimethylaminopyridine (403 mg, 3.3 mmol) and the mixture was refluxed under stirring for 11 hours. After cooling the salt was filtered off and the solvent was distilled off under vacuo and there was obtained methyl 4-azido-3-hydroxybutyrate (5.5 g) as a crude product. And followed by the same procedure as in example 1, there was obtained 4-hydroxy-2-pyrrolidone (2.3 g, 23 mmol, yield:70%). When the above reaction was carried out in the absence of 4-dimethylaminopyridine, it took more than 120 hours to detect the disappearance of the starting materials on gas chromatography.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling the salt
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off under vacuo

Sources & evidence

ORD record
ord-e4bf2c4cf45f45a4a1954e8655437745
Source dataset
uspto-grants-1999_02
Patent number
US05869694

Reaction notes

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