Sodium Azide → HCID 76687305, compound

HRID 588479Notes

Reaction equation

HRID 588479 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][CH:6]1[CH:11](OS(C)(=O)=O)[CH2:10][CH2:9][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7]1>CN(C=O)C.O.C(Cl)Cl>[N:1]([CH:11]1[CH2:10][CH2:9][N:8]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:7][CH:6]1[F:5])=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 454898981,1-Dimethylethyl 3-fluoro-4-[(methylsulfonyl)oxy]-1-piperidinecarboxylate

Product 1

HCID 76687305HCID 76687305, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (68.2 g, 1.050 mol) was added to a solution of tert-butyl 3-fluoro-4-((methylsulfonyl)oxy)piperidine-1-carboxylate, 2.5 (78 g, 0.262 mol) in DMF (620 mL). The reaction mixture was heated at 100° C. for overnight. The mixture was cooled and diluted with 500 mL) water and methylene chloride (500 mL). After separation, the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuum to provide the desired product tert-butyl 4-azido-3-fluoropiperidine-1-carboxylate, 2.6 (62 g, 96% yield), which was used for the next reaction without any purification.

Workup

  1. temperatureThe mixture was cooled
  2. customAfter separation
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-b42fdd820e5e43f49feb9b31d00932a1
Source dataset
uspto-grants-2016_01
Patent number
US09227969B2

Reaction notes

Loading…