HCID 18009445, compound → HCID 18009513, compound

HRID 987596Notes

Reaction equation

HRID 987596 reaction equation
[C:1]1([C:7]2([CH2:14][NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[O:17])[CH2:12][CH2:11][C:10](=[CH2:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCOC(C)=O.[Pd]>[CH3:13][CH:10]1[CH2:11][CH2:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:14][NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[O:17])[CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 18009445HCID 18009445, compound

Product 1

HCID 18009513HCID 18009513, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-phenyl-1-(3-(2-methoxyphenyl)-3-oxo-2-azaprop-1-yl)-4-methylidenecyclohexane (Example 165, 38 mg, 0.11 mmol) and Pd/C (10%, 16.7 mg) in 15 mL of EtOAc was shaken under 50 psi of H2 for 2.5 h. The mixture was filtered through a plug of celite, concentrated and the residue was purified by HPLC (Waters RCM, μ Porosil, 25 mm×10 cm) using a mixture of (5:4:1 hexane-methyl tert-butyl ether-acetonitrile:hexane, 2.0/8.9 mL/min) to afford the two isomers of the title compound.

Workup

  1. filtrationThe mixture was filtered through a plug of celite,
  2. concentrationconcentrated
  3. customthe residue was purified by HPLC (Waters RCM, μ Porosil, 25 mm×10 cm)
  4. additiona mixture of (5:4:1 hexane-methyl tert-butyl ether-acetonitrile:hexane, 2.0/8.9 mL/min)

Sources & evidence

ORD record
ord-54c062ba68a340ec8ad93effc45ad48f
Source dataset
uspto-grants-2003_10
Patent number
US06632836B1

Reaction notes

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