HCID 18770993, compound → HCID 18770915, compound

HRID 1786826Notes

Reaction equation

HRID 1786826 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:10]3([CH2:15][CH2:14][N:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:11]3)[CH:9]=2)=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:10]3([CH2:15][CH2:14][N:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:11]3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18770993HCID 18770993, compound

Product 1

HCID 18770915HCID 18770915, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 4-(4-methylphenyl)spiro[2H-1-benzopyran-2,4′-piperidine]-1′-acetate (730 mg, 0.194 mmol) in ethyl alcohol (125 cm3) was added 10% palladium on carbon. This mixture was heated to 40° C. for 7 h under an atmosphere of hydrogen (4 bar) and then it was filtered whilst still warm and the filter cake was washed with hot ethyl alcohol (3×50 cm3). The solvent was removed in vacuo and the resulting compound was recrystallised from ethyl alcohol (67%). This ester was hydrolysed according to the procedure in Example 1; m.p. 247-249° C.; (M+H)+ =352.2.

Workup

  1. filtrationit was filtered
  2. temperaturewhilst still warm
  3. washthe filter cake was washed with hot ethyl alcohol (3×50 cm3)
  4. customThe solvent was removed in vacuo
  5. customthe resulting compound was recrystallised from ethyl alcohol (67%)

Sources & evidence

ORD record
ord-1376c6eaa9ef4a93b7a9a998d8f2e782
Source dataset
uspto-grants-2009_03
Patent number
US07507824B2

Reaction notes

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