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

HRID 1768595Notes

Reaction equation

HRID 1768595 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7](=[O:25])[CH2:8][CH2:9][C:10](=[CH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:11]([OH:13])=[O:12])[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[O:1]1[CH2:2][CH2:3][N:4]([C:7](=[O:25])[CH2:8][CH2:9][CH:10]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:11]([OH:13])=[O:12])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 538910904-Morpholinocarbonyl-2-(1-naphthylmethylene)butyric acidHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5 g (14.8 mmole) of the 5-morpholino-2-(1-naphthylmethylene)-5-oxopentanoic acid (prepared as described above) were dissolved in 50 ml of methanol and hydrogenated in an atmosphere of hydrogen at atmospheric pressure and in the presence of 1.0 g of a 10% w/w palladium-on-carbon catalyst. The catalyst was then removed by filtration, and 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 5-morpholino-2-(1-naphthylmethyl)-5-oxopentanoic acid as white crystals, melting at 130°-135° C.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe 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-dbe538b0e69740818462049c57e8a4ad
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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