Sodium Azide → 1,1-Dimethylethyl 4-azido-1-piperidinecarboxylate

HRID 1845882Notes

Reaction equation

HRID 1845882 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](CS([O-])(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:19]=[N+:20]=[N-:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 131732428HCID 131732428, compound

Product 1

HCID 114587941,1-Dimethylethyl 4-azido-1-piperidinecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

N-tert-butyloxycarbonyl-4-piperidinemethanesulfonate (10.0 g, 36 mmol) was dissolved in DMF (100 mL), sodium azide (NaN3, 7.0 g, 108 mmol) was added, the reaction mixture was warmed to 100° C., and the reaction was performed overnight. The solvent in the resultant mixture was evaporated under reduced pressure, water (100 mL) and ethyl acetate (100 mL) were added, the organic phase was separated, washed with water (100 mL×2) and saturated brine successively, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to remove ethyl acetate so as to yield the target product as light yellow liquid (8.2 g, 36 mmol; yield=100%). The crude produce was directly used for the reaction in the next step.

Workup

  1. customThe solvent in the resultant mixture was evaporated under reduced pressure, water (100 mL) and ethyl acetate (100 mL)
  2. additionwere added
  3. customthe organic phase was separated
  4. washwashed with water (100 mL×2) and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customto remove ethyl acetate so as

Sources & evidence

ORD record
ord-706c4ee5fab24353afbe951caa1881b1
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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