HCID 19080421, compound → HCID 19080452, compound

HRID 865531Notes

Reaction equation

HRID 865531 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:10]([O:12][CH3:13])=[O:11])=[C:6]([CH2:25][CH:26]=[CH2:27])[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:10]([O:12][CH3:13])=[O:11])=[C:6]([CH2:25][CH2:26][CH3:27])[CH:5]=1

Participants

4

Reactant 1

HCID 19080421HCID 19080421, compound

Product 1

HCID 19080452HCID 19080452, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product of Step B (0.5 g) in methanol (6 mL) was added Pd-C(10%)(0.05g), and the reaction mixture was stirred at room temperature for 6 h under an atmosphere of hydrogen gas. The catalyst was filtered off and the filtrate was concentrated in vacuo to give the desired methyl α-(4-amino-2-n-propylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate (0.5 g) as a solid. This material without further purification was dissolved in dry THF (5 mL) and reacted with N-iso-propylisocyanate (0.1 mL) at room temperature for 12 h. Purification of the crude product by flash chromatography using EtOAc-hexanes (1:2) gave the titled compound as white solid (0.36 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e65caeefd21b4f21b71108a034469857
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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