2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol → Tramadol

HRID 430853

Reaktionsgleichung

C1(C)C=CC(C([C@](C(O)=O)(O)[C@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1.[CH3:29][N:30]([CH2:32][CH:33]1[C:38]([OH:47])([C:39]2[CH:44]=[C:43]([O:45][CH3:46])[CH:42]=[CH:41][CH:40]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1)[CH3:31]>C(O)C>[CH3:31][N:30]([CH2:32][C@@H:33]1[C@@:38]([OH:47])([C:39]2[CH:40]=[CH:41][CH:42]=[C:43]([O:45][CH3:46])[CH:44]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1)[CH3:29]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

The white solid was collected by filtration to give 58.3 g (75.4%) of (L)-(−)-DTTA which compared to an authentic sample. 77.3 g of Di-p-toluoyl-D-tartaric acid ((D)-(+)-DTTA) was taken up in 550 ml of ethanol at 70° C. in a jacketed vessel. To this solution was added the Tramadol free base in 200 ml of ethanol. A precipitate formed almost immediately. The vessel was gradually cooled to 25° C. over several hours to give a fine white solid. Stirring at 25° C. was maintained overnight. The resulting copious white solid was collected at the pump, washing with 500 ml of ethanol. This gave 111.6 g of (+)-Tramadol. Di-p-toluoyl-D-tartaric acid in 85.2% yield, with a de of 97.3%. Reslurrying of this salt from 500 ml of ethanol as above gave 108.5 g of the (+)-Tramadol-containing salt, with a de of >99% in 97.8% yield. [α]D 589=+103.30° (C=1.15, MeOH). MP=162.1-167.8° C. (DSC).

Aufarbeitung

customA precipitate formed almost immediately
customto give a fine white solid
temperaturewas maintained overnight
customThe resulting copious white solid was collected at the pump
washwashing with 500 ml of ethanol

Quellen und Nachweise

ORD-Eintrag: ord-bfb169778fad4603a0f1ef7648eeb019
Quelldatensatz: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06323368B1

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