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

HRID 1017771Notes

Reaction equation

HRID 1017771 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([Sn]([N:29]=[N+:30]=[N-:31])(CCCC)CCCC)CCC>O1CCOCC1>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:31][N:30]=[N:29][N:15]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 4984872Tributyltin azide

Product 1

HCID 18187701Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.513 g of N-Boc 4-cyanopiperidine in 5 mL of dioxane was added 0.71 mL of tri-n-butyl tin azide. The reaction was heated at 100° C. for 4 days and was then evaporated to a viscous oil. The residue was taken up in 5 mL of ether and treated with 10 mL of 2N hydrochloric acid in ether. The reaction was stirred for 1 hour and then the precipitate was filtered, washed well with ether and dried to afford 0.54 g the title compound as a tan solid.

Workup

  1. customwas then evaporated to a viscous oil
  2. additiontreated with 10 mL of 2N hydrochloric acid in ether
  3. filtrationthe precipitate was filtered
  4. washwashed well with ether
  5. customdried

Sources & evidence

ORD record
ord-db505dff35aa4ffca81f04440e590d5d
Source dataset
uspto-grants-2002_11
Patent number
US06479518B2

Reaction notes

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