HCID 86744006, compound → HCID 23047442, compound

HRID 2107086Notes

Reaction equation

HRID 2107086 reaction equation
[OH:1][CH:2](/[CH:12]=[CH:13]/[C:14]1[C:15]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][N:17]2[C:26]=1[CH:27]([CH3:29])[CH3:28])[CH2:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]>C(O)C.[Pd]>[OH:1][CH:2]([CH2:12][CH2:13][C:14]1[C:15]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][N:17]2[C:26]=1[CH:27]([CH3:28])[CH3:29])[CH2:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 86744006HCID 86744006, compound

Product 1

HCID 23047442HCID 23047442, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of ethyl (E)-5-hydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)-3-oxohept-6-enoate (0.94 g; prepared as described in Reference Example 2) in ethanol (42 ml) was reduced catalytically under a hydrogen atmosphere using 5% w/w palladium on charcoal (0.254 g) and 5% w/w palladium on calcium carbonate (0.226 g) as catalysts. The mixture was filtered to remove the catalysts and the filtrate was evaporated, to give ethyl 5-hydroxy-7-(3-isopropyl1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)-3-oxoheptanoate (0.98 g) in the form of a pale green gum.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalysts
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-4cb620aa4dec458381af4cc68aabc339
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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