Benzyl 2-benzyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate → HCID 21970317, compound

HRID 264609Notes

Reaction equation

HRID 264609 reaction equation
[CH2:1]([CH:8]1[CH2:13][C:12](=[O:14])[CH:11]=[CH:10][N:9]1C(OCC1C=CC=CC=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd].[Ni]>[CH2:1]([C@@H:8]1[CH2:13][C@H:12]([OH:14])[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 19035856Benzyl 2-benzyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 21970317HCID 21970317, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

150 g (0.467 mol) of 2-benzyl-N-benzyloxycarbonyl-2,3-dihydro-4-(1H)-pyridone in 1.5 l of methanol are hydrogenated with 7.5 g of Pd/C (10%) as catalyst, then 50 g of Raney nickel and a further 200 ml of methanol are added, and hydrogenation is left to go to completion. Filtration is followed by evaporation in a rotary evaporator, and the brownish oil is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (60:10:1). The title compound is obtained as a semi-crystalline mass which is used further without additional purification. Crystallisation of a sample from ether/hexane yielded white crystals of melting point 111°-112°. TLC: methylene chloride/methanol/conc. ammonia (40:10:1) Rf =0.55, FD-MS: M+ =191.

Workup

  1. waithydrogenation is left
  2. filtrationFiltration
  3. customis followed by evaporation in a rotary evaporator
  4. customthe brownish oil is chromatographed on silica gel with methylene chloride/methanol/conc

Sources & evidence

ORD record
ord-e10f9d64fc834d68ad1e5222b3c6ffe7
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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