HCID 58292877, compound → HCID 58292952, compound

HRID 511213Notes

Reaction equation

HRID 511213 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])([CH3:12])[CH3:11])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]([P:13](=[O:20])([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19])([CH3:12])[CH3:11])=[CH:8][CH:9]=1

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, 6 H), 1.54 (s, 3 H), 1.59 (s, 3 H), 3.65 (s, br, 2 H), 3.80-3.94 (m, 2 H), 6.66 (d, J=8.8 Hz, 2 H), 7.32 (dd, J=2.4, 8.8 Hz, 2 H). 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-48aa05d44b2546a7ba91bcc7fa9c008f
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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