HCID 90952840, compound → HCID 11786040, compound

HRID 1182350Notes

Reaction equation

HRID 1182350 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C@@H:6]([C:32]1[CH:33]=[N:34][C:35]([O:38][CH3:39])=[N:36][CH:37]=1)[CH2:7][C:8](=[O:31])[CH:9]=[CH:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[CH2:22][CH2:21][CH2:20][CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:17]=2[N:30]=1)=[O:4]>C(O)(C)C.[Pd]>[CH3:1][O:2][C:3]([CH2:5][C@@H:6]([C:32]1[CH:33]=[N:34][C:35]([O:38][CH3:39])=[N:36][CH:37]=1)[CH2:7][C:8](=[O:31])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[CH2:22][CH2:21][CH2:20][CH2:19][N:18]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[C:17]=2[N:30]=1)=[O:4]

Participants

4

Reactant 1

HCID 90952840HCID 90952840, compound

Product 1

HCID 11786040HCID 11786040, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent2×

Procedure

The solution of the enone intermediate of Example 9 in isopropanol was charged to a hydrogenation vessel under an atmosphere of nitrogen. A slurry of wet (58 wt % water) palladium on carbon catalyst (1.27 kg) in isopropanol (10 L) was added, washing with further isopropanol (15 L). After degassing the resulting reaction mixture was hydrogenated at 2.8 bar for 2 hours. The catalyst was filtered and washed with isopropanol (4×15 L). The combined filtrates (88.0 kg) were concentrated under reduced pressure to a total volume of ca. 20 L and the solution was directly used in Example 11 without isolation of the product.

Workup

  1. washwashing with further isopropanol (15 L)
  2. customAfter degassing
  3. customthe resulting reaction mixture
  4. filtrationThe catalyst was filtered
  5. washwashed with isopropanol (4×15 L)
  6. concentrationThe combined filtrates (88.0 kg) were concentrated under reduced pressure to a total volume of ca. 20 L

Sources & evidence

ORD record
ord-8e461b8d8c594122bb1464718df8fe66
Source dataset
uspto-grants-2007_10
Patent number
US07288655B2

Reaction notes

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