Sodium Azide → tert-butyl N-(2-azidopropyl)carbamate

HRID 1026865Notes

Reaction equation

HRID 1026865 reaction equation
CS(O[CH:6]([CH3:16])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=O)=O.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.O>[N:17]([CH:6]([CH3:16])[CH2:7][NH:8][C:9](=[O:10])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 231340711-(Tert-butoxycarbonylamino)propan-2-yl methanesulfonate

Product 1

HCID 23122173tert-butyl N-(2-azidopropyl)carbamateYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1-(tert-butoxycarbonylamino)propan-2-yl methanesulfonate (10.0 g, 39.5 mmol) in DMF (100 mL) at RT was added NaN3 (7.7 g, 118.5 mmol). The reaction mixture was stirred at 85° C. for 24 h, cooled to RT, diluted with cold water (300 mL) and extracted with diethyl ether (3×300 mL). The combined organic layers were washed with saturated NaHCO3 (2×200 mL) and brine (200 mL), dried over MgSO4, filtered and concentrated under reduced pressure to afford tert-butyl 2-azidopropylcarbamate (7.0 g, 88.6%) as a light yellow oil. 1HNMR (CDCl3): δ3.6 (m, 1H, CH), 3.25 (m, 1H, CH2), 2.9 (m, 1H, CH2), 1.49 (s, 9H, CH3), 1.2 (d, 3H, CH3).

Workup

  1. temperaturecooled to RT
  2. extractionextracted with diethyl ether (3×300 mL)
  3. washThe combined organic layers were washed with saturated NaHCO3 (2×200 mL) and brine (200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-079f1933e7ad4203b495bbe30f9a6f21
Source dataset
uspto-grants-2014_05
Patent number
US08729293B2

Reaction notes

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