HCID 18009485, compound → HCID 18009425, compound

HRID 987605Notes

Reaction equation

HRID 987605 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:11][CH2:10][C:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH2:12][NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[O:15])[CH2:8][CH:7]=1)(=[O:3])[CH3:2].[H][H]>CCOC(C)=O.[Pd]>[C:1]([O:4][CH2:5][CH:6]1[CH2:7][CH2:8][C:9]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([CH2:12][NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[O:15])[CH2:10][CH2:11]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 18009485HCID 18009485, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18009425HCID 18009425, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-acetoxymethyl-4-phenyl-4-(3-(2-methoxyphenyl)-3-oxo-2-azaprop-1-yl)-cyclohex-1-ene (Example 200, 11.5 mg, 0.029 mmol) in 5 mL of EtOAc was shaken with Pd/C (5 mg, 10%) under 50 psi of hydrogen for 14 h. The mixture was filtered through silica gel, concentrated and 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, 4.5/8.0 mL/min) to give the 2 isomers of the title compound

Workup

  1. filtrationThe mixture was filtered through silica gel
  2. concentrationconcentrated
  3. custompurified by HPLC (Waters RCM, μ Porosil, 25 mm×10 cm)
  4. additiona mixture of (5:4:1 hexane-methyl tert-butyl ether-acetonitrile:hexane, 4.5/8.0 mL/min)

Sources & evidence

ORD record
ord-29a361dae1c5485488a7229b1dba5588
Source dataset
uspto-grants-2003_10
Patent number
US06632836B1

Reaction notes

Loading…