HCID 178418361, compound → HCID 178490122, compound

HRID 2225552Notes

Reaction equation

HRID 2225552 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([CH:11]=[CH:12][CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[C:17]([O:29][CH3:30])[CH:16]=2)=[O:10])[CH2:4][CH2:3]1.[H][H]>CO.[C].[Pd]>[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:10])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:29][CH3:30])[CH:16]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178490123HCID 178490123, compound

Product 1

HCID 178490122HCID 178490122, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3.62 g of N-(trans-4-methylcyclohexyl)-4-(4-benzyloxy-3-methoxyphenyl)-l,3-butadiene-1-carboxamide (Example 117) was dissolved in 150 ml of methanol. 0.2 g of 10% palladium-carbon was added to the solution. The solution was stirred for 16 hours under normal-pressure hydrogen gas. After reaction, the catalyst was filtered out, and the solvent was removed in vacuo from the filtrate, yielding 2.3 g of N-(trans-4-methylcyclohexyl)-5-(4-hydroxy-3-methoxyphenyl)valeramide (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customAfter reaction
  2. filtrationthe catalyst was filtered out
  3. customthe solvent was removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-e10504eca05e454e900f09859108711d
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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