Sulfuric Acid → (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl-pentan-3-yl 4-methylbenzenesulfonate

HRID 534700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534700
[CH3:1][N:2]([CH3:18])[CH2:3][C@H:4]([CH3:17])[C@:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)([OH:8])[CH2:6][CH3:7].S(=O)(=O)(O)O.CS(O)(=O)=O.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](O)(=[O:37])=[O:36])=[CH:31][CH:30]=1.[OH-].[Na+]>C1CCCCC1.O1CCCC1>[CH3:39][C:29]1[CH:34]=[CH:33][C:32]([S:35]([O:8][C@:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)([CH2:6][CH3:7])[C@@H:4]([CH3:17])[CH2:3][N:2]([CH3:1])[CH3:18])(=[O:37])=[O:36])=[CH:31][CH:30]=1

Komponenten

8

Edukt 5

HCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 9942979(alphaR)-alpha-[(1S)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanol

Produkt 1

HCID 56832993(2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl-pentan-3-yl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8078CyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Accordingly the compound (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol of Formula-V was charged in the solvent tetrahydrofuran and under stirring charged concentrated sulfuric acid at temperature of 20-30° C. The reaction mixture is stirred and charged methanesulfonic acid or para toluenesulfonic acid and solvent cyclohexane. Stirred and raised the temperature to reflux. Maintained the reaction mass at reflux temperature for 3-5 hours with simultaneous removal of water. Cooled the reaction mass to 20° C. and quenched with water. The pH of the quenched reaction solution was adjusted to 8-9 using dilute sodium hydroxide solution. The reaction solution was extracted with cyclohexane. Separated the organic layer and concentrated under reduced pressure to get the compound (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-yl methane sulfonate of Formula IXA or (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl-pentan-3-yl 4-methylbenzenesulfonate of Formula IXB.

Aufarbeitung

  1. stirringThe reaction mixture is stirred
  2. stirringStirred
  3. temperatureraised the temperature
  4. temperatureto reflux
  5. temperatureMaintained the reaction mass
  6. temperatureat reflux temperature for 3-5 hours
  7. customwith simultaneous removal of water
  8. customquenched with water
  9. customThe pH of the quenched reaction solution
  10. extractionThe reaction solution was extracted with cyclohexane
  11. customSeparated the organic layer
  12. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ea248a4580344c1b8f17e9ed117ceaeb
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853456B2

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