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

HRID 1095727Notes

Reaction equation

HRID 1095727 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C@H:6]1[C@H: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]([C@H:11]1[CH2:10][CH2:9][N:8]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:7][C@H:6]1[F:5])=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 52324471HCID 52324471, compound

Product 1

HCID 121592108Tert-butyl cis-4-azido-3-fluoro-piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

Sodium azide (4.045 g, 62.22 mmol) was added to a solution of (trans)-tert-butyl 3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylate (3.700 g, 12.44 mmol) dissolved in DMF (25 mL). The reaction was heated to 115° C. for 24 hours. The mixture was cooled and diluted with water and methylene chloride. After separation, the organic layer was dried over Na2SO, filtered and concentrated in vacuo to provide the desired product (quantitative yield).

Workup

  1. temperatureThe mixture was cooled
  2. customAfter separation
  3. dry with materialthe organic layer was dried over Na2SO
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fbc656051524f20aa5cd4c6cddec8ac
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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