Ethanol → HCID 22257800, compound

HRID 324576Notes

Reaction equation

HRID 324576 reaction equation
[CH3:1][C:2]([CH3:26])([CH2:24][CH3:25])[C:3](=[O:23])[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11](=[O:22])[CH2:12][CH2:13][CH:14]=[CH:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:5].C(OCC)(=O)C.C(O)C.C(O)C.C(OCC)(=O)C>CO.[Pt]=O.[Pd]>[CH3:1][C:2]([CH3:26])([CH2:24][CH3:25])[C:3](=[O:23])[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11](=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:5]

Participants

8

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 21584252Ethanol ethylacetateHCID 69663375HCID 69663375, compound

Product 1

HCID 22257800HCID 22257800, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent2×

Procedure

Platinum oxide (12 mg) was added to a solution of 3,3-dimethyl-1-[2-(5-(3-pyridyl)pent-4-enoyl)pyrrolidinyl]pentane-1,2-dione (300 mg; 0.84 mmol) in methanol (8 ml). The mixture was hydrogenated at 1 atm. for 2.5 hours. TLC indicated that the reaction was complete, and it was filtered through Celite and concentrated. Eluting through a plug of silica gel (ethyl acetate) furnished analytically pure material, 260 mg (87%). 1 H NMR (CDCl3, 400 MHz): δ0.87 (t, 3H, J=7.5); 1.21 (s, 6H); 1.64 (m, 4H); 1.69 (m, 2H); 1.78 (m, 1H); 1.96 (m, 2H); 2.15 (m, 1H); 2.53 (m, 1H); 2.63 (m, 2H); 3.49 (m, 1H); 3.53 (m, 1H); 4.57 (dd, 1H, J=8.8, 4.8); 7.20 (m, 1H); 7.49 (m, 1H, J=7.8); 8.44 (m, 2H). Anal. Calcd. for C21H30N2O3: C, 70.36; H, 8.44; N, 7.81. Found: C, 70.15; H, 8.54; N, 7.76. TLC: R1=0.80 (ethyl acetate:ethanol 4:1). Note: this final hydrogenation step may be done using 10% Pd/C, and hydrogenating for 5 hours at 60 psi. Ethanol or ethyl acetate may be used instead of methanol.

Workup

  1. filtrationit was filtered through Celite
  2. concentrationconcentrated
  3. washEluting through a plug of silica gel (ethyl acetate)
  4. customfurnished analytically pure material, 260 mg (87%)
  5. customfor 5 hours

Sources & evidence

ORD record
ord-71b67275b66d4b13ac25827110778d1b
Source dataset
uspto-grants-2001_04
Patent number
US06218424B1

Reaction notes

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