HCID 58292877, compound → HCID 58292952, compound

HRID 1947786Notes

Reaction equation

HRID 1947786 reaction equation
[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>CO.[Pd]>[CH2:6]([O:5][P:4]([C:9]([C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)([CH3:10])[CH3:11])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 1

HCID 58292877HCID 58292877, compound

Product 1

HCID 58292952HCID 58292952, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The diethyl[2-(4-nitrophenyl)propan-2-yl]phosphonate (103 mg) prepared as described above, was hydrogenated in the presence of 10% Pd/C (50 mg) in MeOH (5 mL) for 4 h. The mixture was filtered and the filtrate concentrated in vacuo to afford 92.5 mg of the desired diethyl[2-(4-aminophenyl)propan-2-yl]phosphonate (yield: 99%), which was used in further chemistries without purification. 1H-NMR (CDCl3, 400 MHz): δ=1.20 (t, J=7.2 Hz, 6H), 1.54 (s, 3H), 1.59 (s, 3H), 3.65 (s, br, 2H), 3.80-3.94 (m, 2H), 6.66 (d, J=8.8 Hz, 2H), 7.32 (dd, J=2.4, 8.8 Hz, 2H). MS (ES+): m/z 272.02 (MH+). HPLC: tR=2.45 min (ZQ3, polar—5 min).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-d2948a3d5794416bb5edd33b3fb02c2f
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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