Diethyl 3-azidopropylphosphonate → Diethyl (3-aminopropyl)phosphonate

HRID 2204946Notes

Reaction equation

HRID 2204946 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[N+]=[N-].[H][H]>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][CH2:5][CH2:6][P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 10867835Diethyl 3-azidopropylphosphonateHCID 178418361HCID 178418361, compound

Product 1

HCID 78113Diethyl (3-aminopropyl)phosphonate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Diethyl 3-azidopropylphosphonate (1 eq) was dissolved in EtOH (0.1 M). Pd(OH)2 (0.02 eq) was added to the reaction. Hydrogen gas was introduced via a balloon and the reaction was stirred for 3 hours. The reaction was stirred for a further 2 hours at room temperature and filtered through Celite and washed with methanol. The solvent was removed en vaccuo and the crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH in DCM with 0.5% NH3 in MeOH to give the product as colorless oil.

Workup

  1. stirringThe reaction was stirred for a further 2 hours at room temperature
  2. filtrationfiltered through Celite
  3. washwashed with methanol
  4. customThe solvent was removed en vaccuo
  5. customthe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-099c99ae961c4daaa6ca591a6d14e6fb
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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