Sodium Azide → Tert-butyl n-[1-(azidomethyl)undecyl]-carbamate

HRID 970301Notes

Reaction equation

HRID 970301 reaction equation
I[CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 88159309Tert-butyl n-[1-(r/s)-(iodomethyl)undecyl]carbamate

Product 1

HCID 91612995Tert-butyl n-[1-(azidomethyl)undecyl]-carbamateYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

tert-Butyl N-[1-(R/S)-(iodomethyl)undecyl]carbamate 62 (250 mg, 0.608 mmol) was dissolved in abs. DMF (10 ml). Sodium azide (79.0 mg, 1.22 mmol) was added to the solution, which was subsequently stirred at 110° C. for 12 hours. Following evaporation, the residue was taken up in CH2Cl2 (50 ml) and was washed with NaHCO3(sat, aq) (1×50 ml). The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography in hexane:ether 10:1 (v/v) to give 63 (100 mg, 54%).

Workup

  1. customevaporation
  2. washwas washed with NaHCO3(sat, aq) (1×50 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography in hexane:ether 10:1 (v/v)

Sources & evidence

ORD record
ord-d7cd17848bf745a6b01ac0d5450456bf
Source dataset
uspto-grants-2007_12
Patent number
US07312194B2

Reaction notes

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