HCID 86654034, compound → HCID 86654033, compound

HRID 1947986Notes

Reaction equation

HRID 1947986 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][P:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)(=[O:12])[O:7][CH2:8][CH2:9][O:10][CH3:11].[H][H]>CCO.[Pd]>[CH3:11][O:10][CH2:9][CH2:8][O:7][P:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)(=[O:12])[O:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

5

Reactant 2

HCID 86654034HCID 86654034, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86654033HCID 86654033, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of bis(2-methoxyethyl)(4-nitrobenzyl)phosphonate (Compound 185B, 6.0 g, 18 mmol) and 5% Pd/C (0.8 g) in EtOH (150 mL) was hydrogenated under 40 psi hydrogen pressure at 40° C. for 6 h. The reaction mixture was filtered and the filtrate was concentrated to give the desired product (5.3 g, 97%). 1H NMR (CDCl3, 400 MHz): δ=3.04 (d, J=21.2 Hz, 2H), 3.28 (s, 6H), 3.42-3.46 (m, 4H), 3.97-4.03 (m, 4H), 6.55 (d, J=8.4 Hz, 2H), 6.99-7.02 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-704868b318874d699468cc003c4107b0
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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