HCID 86678260, compound → HCID 86678261, compound

HRID 2204949Notes

Reaction equation

HRID 2204949 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[N+]=[N-].[H][H]>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][P:9](=[O:16])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 86678260HCID 86678260, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86678261HCID 86678261, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Diethyl 2-(2-azidoethoxy)ethylphosphonate (1 eq) was dissolved in EtOH (0.1 M). Pd(OH)2 (0.05 eq) was added to the reaction. Hydrogen gas was introduced via a balloon; and the reaction was stirred for 2 hours at room temperature. The mixture was filtered through Celite and washed with MeOH. The solvent was removed en vaccuo and the crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM with 2% NH3 in methanol to give the product as colorless oil.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with MeOH
  3. customThe solvent was removed en vaccuo
  4. customthe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-1bacff7ebe3446158d73f43952698e7c
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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