Triethylamine → 2,2-Dimethyl-1-(2-hydroxyethyl)-7-methoxy-3-(N-methyl-p-toluenesulphonamido)-1,2,3,4-tetrahydronaphthalene

HRID 2287049Notes

Reaction equation

HRID 2287049 reaction equation
[CH3:1][C:2]1([CH3:29])[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][OH:28].C(N(CC)CC)C.[H][H]>CO.[Pd]>[CH3:1][C:2]1([CH3:29])[CH:11]([N:12]([CH3:23])[S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=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][OH:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 54324160HCID 54324160, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 539916072,2-Dimethyl-1-(2-hydroxyethyl)-7-methoxy-3-(N-methyl-p-toluenesulphonamido)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,2-Dimethyl-1-(2-hydroxyethylidene)-7-methoxy-3-(N-methyl-p-toluenesulphonamido)-1,2,3,4-tetrahydronaphthalene (15.5 g), dissolved in 250 ml of methanol, containing 2.2 ml of triethylamine, is submitted to catalytic hydrogenation, at atmosphere pressure and room temperature, the catalyst being 2.3 g 5% palladium on charcoal. The calculated amount of hydrogen is taken up within one hour. The catalyst is removed by filtration and the solvent by evaporation in vacuo. The residue is dissolved in chloroform and the solution is freed from basic material by means of washing with dilute hydrochloric acid and water, respectively. The dried solution is then concentrated in vacuo leaving a mixture containing two stereoisomers of the desired product. This mixture is suitable for further elaboration as described in example 13.

Workup

  1. customis submitted to catalytic hydrogenation, at atmosphere pressure and room temperature
  2. customThe catalyst is removed by filtration
  3. customthe solvent by evaporation in vacuo
  4. dissolutionThe residue is dissolved in chloroform
  5. washof washing with dilute hydrochloric acid and water
  6. concentrationThe dried solution is then concentrated in vacuo
  7. customleaving a mixture

Sources & evidence

ORD record
ord-d52ab9cf60294d70ab6979a57adbd899
Source dataset
uspto-grants-1981_05
Patent number
US04268673

Reaction notes

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