Sodium Azide → HCID 15550580, compound

HRID 2268945Notes

Reaction equation

HRID 2268945 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17]OS(C)(=O)=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][N:23]=[N+:24]=[N-:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 15550579HCID 15550579, compound

Product 1

HCID 15550580HCID 15550580, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Dissolved 1-benzyloxycarbonyl-3-methanesulfonyloxymethyl-piperidine (5.24 mmol, 1 eq) in DMF (50 mL). Added sodium azide (1.7 g, 26.2 mmol, 5 eq). Warmed the mixture to 60° C. and let stir overnight. Removed the DMF under reduced pressure. Diluted the residue with ethyl acetate and washed with water and then brine. Dried the organic layer over anhydrous Na2SO4, filtered and concentrated giving 1.27 g. crude product.

Workup

  1. customRemoved the DMF under reduced pressure
  2. additionDiluted the residue with ethyl acetate
  3. washwashed with water
  4. dry with materialDried the organic layer over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customgiving 1.27 g

Sources & evidence

ORD record
ord-4524cb058cb74de9bab18a828d2c6655
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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