Triethylamine → tert-Butyl (2-azidoethyl)carbamate

HRID 2366874Notes

Reaction equation

HRID 2366874 reaction equation
O[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CCOCC>[N:24]([CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[N+:25]=[N-:26]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 22323692tert-Butyl (2-azidoethyl)carbamateYield 26.6%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1,1-dimethylethyl (2-hydroxyethyl)carbamate (1.483 g, 9.2 mmol) in toluene (40 mL) cooled with an ice bath was added triethylamine (1.282 mL, 9.20 mmol) then methanesulfonyl chloride (0.717 mL, 9.20 mmol) and the resulting mixture was stirred for 5 min at this temperature then tetrabutylammonium bromide (0.297 g, 0.920 mmol) was added followed by a solution of sodium azide (5 g, 77 mmol) in water (20 mL). The resulting mixture was stirred at 60° C. for 3 h then cooled to room temperature and diluted with Et2O (150 mL). The organic layer was washed with water then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 50G silica cartridge gave 1,1-dimethylethyl (2-azidoethyl)carbamate (456 mg, 2.449 mmol, 26.6% yield) as a colourless oil.

Workup

  1. temperaturethen cooled to room temperature
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by SP4

Sources & evidence

ORD record
ord-6c6af382fcc0422683c0b85bcbe2d790
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…