Sodium Azide → tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate

HRID 896511Notes

Reaction equation

HRID 896511 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14]OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:20]=[N+:21]=[N-:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22647269tert-Butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Product 1

HCID 22647380tert-Butyl 3-(azidomethyl)piperidine-1-carboxylateYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3-methanesulfonyloxymethylpiperidine-1-carboxylic acid tert-butyl ester (19.11 g, 65.1 mmol) in N,N-dimethylformamide (125 mL) was treated with sodium azide (12.70 g, 195 mmol) and the mixture was stirred at 50° C. for 22 hours. The mixture was cooled and filtered, and the filtrate was concentrated under vacuum. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulfate, and concentrated under vacuum to provide a colorless liquid (15.34 g, 98%) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ3.95 (bd, J=12 Hz, 1H), 3.86 (dt, J=13, 4 Hz, 1H), 3.22 (d, J=7 Hz, 2H), 2.87 (ddd, J=14, 11, 3 Hz, 1H), 2.68 (m, 1H), 1.9-1.6 (3H), 1.49 (m, 1H), 1.47 (s, 9H), 1.26 (m, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-43f9ce1bc4a74c4cbd651f79cf06b34c
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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