Sodium Azide → HCID 72447677, compound

HRID 402060Notes

Reaction equation

HRID 402060 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][N:27]=[N+:28]=[N-:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86657827HCID 86657827, compound

Product 1

HCID 72447677HCID 72447677, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 4-hydroxy-3-(toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (8.56 mmol, 3.3 g) in DMF (20 mL) was added sodium azide (35.28 mmol, 2.34 g), and the reaction mixture was stirred at 80-90° C. for 16 h. The reaction mixture was cooled to room temperature, diluted with DCM (200 mL), washed with water, and the organic layer was dried and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography by eluting with ethyl acetate in hexanes (1:1) to provide 3-azidomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. customthe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography
  6. washby eluting with ethyl acetate in hexanes (1:1)

Sources & evidence

ORD record
ord-914c66b2307f4884aa5aa8f57bfe4827
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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