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

HRID 1713034Notes

Reaction equation

HRID 1713034 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][N:12]=[N+]=[N-])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>CO.[Pd]>[CH2:6]([O:5][P:4]([CH2:9][CH2:10][CH2:11][NH2:12])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 1

HCID 10867835Diethyl 3-azidopropylphosphonate

Product 1

HCID 78113Diethyl (3-aminopropyl)phosphonateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(3-Azidopropyl)phosphonic acid diethyl ester (240 mg, 1.08 mmol) and activated Pd/C (20 mg) were suspended in methanol (50 ml) and stirred under H2 atmosphere at 40 psi for 3 hours. The black suspension was filtered on Celite, and the solvent was removed under vacuum to give pure (3-aminopropyl)phosphonic acid diethyl ester (205 mg, 99% yield).

Workup

  1. filtrationThe black suspension was filtered on Celite
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2717b228a2b1462caab119ef172393b5
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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