Sodium Azide → Tert-butyl trans-4-azido-3-fluoro-piperidine-1-carboxylate

HRID 588484Notes

Reaction equation

HRID 588484 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C@@H:6]1[C@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][CH2:9][N:8]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:7]1>CN(C=O)C.O.C(Cl)Cl>[N:1]([C@H:11]1[CH2:10][CH2:9][N:8]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:7][C@@H:6]1[F:5])=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 102226241tert-butyl (3S,4R)-3-fluoro-4-(tosyloxy)piperidine-1-carboxylate

Product 1

HCID 58073560Tert-butyl trans-4-azido-3-fluoro-piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (0.48 g, 0.0073 mol) was added to a solution of tert-butyl (3S,4R)-3-fluoro-4-(tosyloxy)piperidine-1-carboxylate, 4.3-1, Peak-1 (0.7 g, 0.00187 mol) dissolved in DMF (15 mL). The reaction mixture was heated at 100° C. for 4 h. The mixture was cooled and diluted with water and methylene chloride. After separation, the organic layer was dried over Na2SO4, filtered and concentrated in vacuum to provide the desired product, 4.4 (0.4 g). The obtained product was taken for the next reaction without any purification.

Workup

  1. temperatureThe mixture was cooled
  2. customAfter separation
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-1f1d426e3f3d4610b7589422856efd69
Source dataset
uspto-grants-2016_01
Patent number
US09227969B2

Reaction notes

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