HCID 69663864, compound → HCID 9820896, compound

HRID 324578Notes

Reaction equation

HRID 324578 reaction equation
[CH3:1][C:2]([CH3:34])([CH2:32][CH3:33])[C:3](=[O:31])[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11](=[O:30])[CH2:12][CH2:13][CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22]CC2C=CC=CC=2)=[CH:18][CH:17]=1)=[O:5]>C(OCC)(=O)C.[Pd]>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][CH2:13][CH2:12][C:11]([CH:7]2[CH2:8][CH2:9][CH2:10][N:6]2[C:4](=[O:5])[C:3](=[O:31])[C:2]([CH3:1])([CH3:34])[CH2:32][CH3:33])=[O:30])=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 69663864HCID 69663864, compound

Product 1

HCID 9820896HCID 9820896, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.63 g (3.53 mmol) of 3,3-dimethyl-1-(2-{5-[4-(phenylmethoxy)phenyl]pent-4-enoyl}pyrrolidinyl)pentane-1,2-dione and 400 mg of 10% Pd/C in 100 ml of ethyl acetate was hydrogenated at 50 psi overnight. The mixture was filtered through Celite, concentrated, and chromatographed (25% ethyl acetate/hexane) to obtain 800 mg (61%) of 1-{2-[5-(4-hydroxyphenyl)pentanoyl]pyrrolidinyl}-3,3-dimethylpentane-1,2-dione (68). 1H NMR (CDCl3, 400 MHz): δ0.87 (t, 3H, J=7.50); 1.21 (s, 6H); 1.63 (m, 4H); 1.67 (m, 2H); 1.93 (m, 3H); 2.04 (m, 1H); 2.52 (m, 4H); 3.47 (m, 2H); 4.57 (m, 1H); 6.72 (d, 2H, J=8.40); 7.03 (d, 2H, J=8.40). Anal. Calcd. for C22H31NO4: C, 70.75; H, 8.37; N, 3.75. Found: C, 70.64; H, 8.44; N, 3.65. TLC: Rf=0.45 (25% ethyl acetate/hexane).

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationThe mixture was filtered through Celite
  3. concentrationconcentrated
  4. customchromatographed (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cdcc8f0aff9c48f5aa6490e566bc531a
Source dataset
uspto-grants-2001_04
Patent number
US06218424B1

Reaction notes

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