Sodium Azide → 3-Azido-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester

HRID 897258Notes

Reaction equation

HRID 897258 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9](OS(C)(=O)=O)[CH2:10]2)=[O:5])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:19]=[N+:20]=[N-:21])[CH2:10]2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 583468803-Methanesulfonyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester

Product 1

HCID 583468423-Azido-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl esterYield 100.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-methanesulfonyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (1.74 g, 6.28 mmol) in DMF (62 mL) was added sodium azide (813 mg, 12.5 mmol) portion-wise. The mixture was heated to 100° C., stirred for 5 hrs, cooled, and diluted with ethyl acetate. The solution was washed three times with water, sodium bicarbonate, brine; dried over Na2SO4, filtered, and concentrated to provide a yellow oil (1.42 g). 1H NMR (300 MHz, CDCl3) δ ppm 1.25 (t, J=7.1 Hz, 3H), 1.68 (m, 4H), 1.91 (m, 2H), 2.01 (m, 2H), 3.73 (m, 1H), 4.15 (q, J=7.0 Hz, 2H), 4.34 (m, 2H); MS (ESI+Q1MS) m/z 225 [M−H]+

Workup

  1. temperaturecooled
  2. washThe solution was washed three times with water, sodium bicarbonate, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-130e71bcfcfe48858396d6edceca6d96
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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