HCID 86654034, compound → HCID 86654033, compound

HRID 511415Notes

Reaction equation

HRID 511415 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]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][P:6](=[O:12])([O:5][CH2:4][CH2:3][O:2][CH3:1])[O:7][CH2:8][CH2:9][O:10][CH3:11])=[CH:19][CH:18]=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, 2 H), 3.28 (s, 6 H), 3.42-3.46 (m, 4 H), 3.97-4.03 (m, 4 H), 6.55 (d, J=8.4 Hz, 2 H), 6.99-7.02 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-37577efa0ea346519f94b3118b5a5565
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

Loading…