HCID 88427648, compound → HCID 19023596, compound

HRID 1034228Notes

Reaction equation

HRID 1034228 reaction equation
O[N:2]=[C:3]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH:4]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>CCO.[Pd]>[NH2:2][CH:3]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH:4]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

4

Reactant 1

HCID 88427648HCID 88427648, compound

Product 1

HCID 19023596HCID 19023596, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of oxime of Example N (3.08 g, 10.6 mmol) in EtOH (80 ml) was hydrogenated at 1000 psi at 70° C. on 10% palladium on carbon. Filtration and concentration of the filtrate gave an oil which was chromatographed on silica gel eluting with 2/97.75/0.25 EtOH/CH2Cl2 /NH4OH to afford the title compound (1.76 g, 60%) as a white solid. Anal calcd for C15H20N2O3 : C, 65.20; H, 7.30; N, 10.14. Found: C, 64.95; H, 7.39; N, 10.04. MS Calcd for C15H20N2O3 276, found 276. DSC=105.0°-121.1° at 57.2 J/g.

Workup

  1. filtrationFiltration and concentration of the filtrate
  2. customgave an oil which
  3. customwas chromatographed on silica gel eluting with 2/97.75/0.25 EtOH/CH2Cl2 /NH4OH

Sources & evidence

ORD record
ord-02ef4759c6d247c5a63ce8af282a2088
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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