HCID 66734647, compound → HCID 66732040, compound

HRID 1963114Notes

Reaction equation

HRID 1963114 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:3]1>CCOC(C)=O.[Pd]>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 66734647HCID 66734647, compound

Product 1

HCID 66732040HCID 66732040, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-oxo-2-phenethyl-3,4-dihydropyridine-1(2H)-carboxylate (21.7 g, ca 75 mmol) was hydrogenated over Pd/C (5%) in EtOAc at 5 bar for 20 h. The mixture was filtered through a silica plug and then evaporated to give the product as an oil (19.8 g). 1H NMR (600 MHz, cdcl3) δ 1.69 (m, 1H), 1.80 (m, 1H), 2.26 (m, 2H), 2.41 (m, 1H), 2.47-2.70 (m, 3H), 3.16 (m, 1H), 3.69 (m, 3H), 4.15-4.48 (br m, 2H), 7.14-7.30 (m, 5H). MS 262 m/z (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a silica plug
  2. customevaporated

Sources & evidence

ORD record
ord-915b1a8daa89452eb78117b93c2d8847
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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