Sodium Azide → HCID 14347788, compound

HRID 2232085Notes

Reaction equation

HRID 2232085 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([CH2:14]S(C)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CO.O>[CH2:1]([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([CH2:14][N:19]=[N+:20]=[N-:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 14347787HCID 14347787, compound

Product 1

HCID 14347788HCID 14347788, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

1-Benzyl-4-hydroxy-3-methanesulfonylmethylpyrrolidine (80.8 g) is added to methanol-water (3:2) (1 liter), and thereto is added dropwise sodium azide (24.5 g), and the mixture is refluxed for 24 hours. After the reaction, the mixture is concentrated and extracted with dichloromethane. The dichloromethane solution is washed with water and saturated saline, dried and concentrated to give 1-benzyl-4-hydroxy-3-azidomethylpyrrolidine (59.7 g) as an oil.

Workup

  1. temperaturethe mixture is refluxed for 24 hours
  2. customAfter the reaction
  3. concentrationthe mixture is concentrated
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane solution is washed with water and saturated saline
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fea7f18239074fdd98a287d80d88940a
Source dataset
uspto-grants-1988_11
Patent number
US04786649

Reaction notes

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