4-Morpholinocarbonyl-2-(1-naphthylmethylene)butyric acid → 4-Morpholinocarbonyl-2-(1-naphthylmethyl)butyric acid

HRID 1768600Notes

Reaction equation

HRID 1768600 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([CH2:9][CH2:10][C:11](=[CH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[C:12]([OH:14])=[O:13])=[O:8])[CH2:3][CH2:2]1>CO.[H][H].[Pd]>[O:1]1[CH2:6][CH2:5][N:4]([C:7]([CH2:9][CH2:10][CH:11]([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[C:12]([OH:14])=[O:13])=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 538910904-Morpholinocarbonyl-2-(1-naphthylmethylene)butyric acid

Product 1

HCID 189483864-Morpholinocarbonyl-2-(1-naphthylmethyl)butyric acidYield 89.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

5.0 g (14.8 mmole) of this 4-morpholinocarbonyl-2-(1-naphthylmethylene)butyric acid were dissolved in 50 ml of methanol and hydrogenated in hydrogen at atmospheric pressure in the presence of 1.0 g of a 10% w/w palladium-on-carbon catalyst. The catalyst was then removed by filtration, after which the solvent was removed by distillation under reduced pressure. The residue was triturated with diethyl ether to precipitate crystals, which were collected by filtration to give 4.5 g of 4-morpholinocarbonyl-2-(1-naphthylmethyl)butyric acid, melting at 130°-135° C.

Workup

  1. customThe catalyst was then removed by filtration
  2. customafter which the solvent was removed by distillation under reduced pressure
  3. customThe residue was triturated with diethyl ether
  4. customto precipitate crystals, which
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3d245a3a6f484597b9260f19441a7177
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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