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

HRID 919140Notes

Reaction equation

HRID 919140 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:12]S([O-])(=O)=O)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.O>[N:17]([CH:10]([CH3:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86671104HCID 86671104, compound

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-ylmethanesulfonate (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-c9ae7d1fcb6b474b8f0c1927bfdd0408
Source dataset
uspto-grants-2016_03
Patent number
US09272984B2

Reaction notes

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