HCID 19978928, compound → HCID 19978936, compound

HRID 1084643Notes

Reaction equation

HRID 1084643 reaction equation
[C:1]([O:4][C:5]1[CH2:9][N:8]([C:10]([CH3:18])([CH3:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:19])[C:6]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:3])[CH3:2]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]([O:4][CH:5]1[CH2:9][N:8]([C:10]([CH3:18])([CH3:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:19])[CH:6]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 19978928HCID 19978928, compound

Product 1

HCID 19978936HCID 19978936, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

6.4 g (20 mmol) of 4-acetoxy-1-(α,α-dimethylbenzyl)-2-oxo-3-phenyl-3-pyrroline prepared by the method of reference Example 14, was dissolved in 100 ml of methanol and subjected to hydrogenation at normal temperature under atmospheric pressure by an addition of 0.4 g of Pd-BaSO4. After completion of the reaction, the catalyst was removed by filtration, and methanol was distilled off. The residue was purified by silica gel column chromatography to obtain 1.0 g (yield: 15%) of the desired compound.

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed by filtration, and methanol
  3. distillationwas distilled off
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c4fc3ca2b58d47ebb982f0111b896e9e
Source dataset
uspto-grants-1991_04
Patent number
US05006157

Reaction notes

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