HCID 53884968, compound → HCID 54375837, compound

HRID 2287048Notes

Reaction equation

HRID 2287048 reaction equation
[CH3:1][C:2]1([CH3:35])[CH:11]([N:12]([CH3:23])[S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:24][CH3:25])=[CH:7][CH:8]=2)[C:3]1=[CH:26][CH2:27][O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1>O1CCOCC1.[Pd]>[CH3:1][C:2]1([CH3:35])[CH:11]([N:12]([CH3:23])[S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:24][CH3:25])=[CH:7][CH:8]=2)[CH:3]1[CH2:26][CH2:27][O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1

Participants

4

Reactant 1

HCID 53884968HCID 53884968, compound

Product 1

HCID 54375837HCID 54375837, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

2,2-Dimethyl-7-methoxy-3-(N-methyl-p-toluenesulphonamido)-1-[2-(tetrahydro-2-pyranyloxy)ethylidene]-1,2,3,4-tetrahydronaphthalene (151 g), dissolved in 1100 ml of dioxan is submitted to a catalytic hydrogenation at atmospheric pressure and roomtemperature, the catalyst being 10 g of 5% palladium on charcoal. After some 80 percent of the calculated amount of hydrogen has been consumed, the hydrogen uptake tends to slow down and an additional quantity of 2 g of catalyst is needed to bring the reduction to an end. The catalyst is removed by filtration and the filtrate is evaporated in vacuo. The residue does not tend to crystallize. It contains a mixture of two stereoisomers of the title product and it is applied without purification in the next synthesis.

Workup

  1. customAfter some 80 percent of the calculated amount of hydrogen has been consumed
  2. customThe catalyst is removed by filtration
  3. customthe filtrate is evaporated in vacuo
  4. customto crystallize
  5. additiona mixture of two stereoisomers of the title product and it
  6. customis applied without purification in the next synthesis

Sources & evidence

ORD record
ord-2cd9f563e097461b841756905f54bd1b
Source dataset
uspto-grants-1981_05
Patent number
US04268673

Reaction notes

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