Sodium Azide → Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylate

HRID 1804600Notes

Reaction equation

HRID 1804600 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)#[N:6]>CN(C=O)C.C(OCC)(=O)C>[NH:1]1[C:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:6][N:3]=[N:2]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylate

Product 1

HCID 18187701Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium azide (228 mg, 3.50 mmol) was added to a stirred, cooled RT mixture of tert-butyl 4-cyanopiperidine-1-carboxylate (243 mg, 1.167 mmol) in DMF (5 ml) and the mixture was stirred at 100° C. for 48 h. The mixture was cooled, diluted with ethyl acetate (100 mL), washed with brine (3×50 mL), dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with 10% methanol in dichloromethane to afford the title compound (197 mg, 75%) as a colorless liquid. ESI-MS calculated for C11H19N5O2: Exact Mass: 253.13. Found 254.12.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with brine (3×50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel Biotage 40S
  7. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-93d1568f477f4028ab1ed60ca940e88b
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

Loading…