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

HRID 430853

반응식

HRID 430853 반응식
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]

참가 물질

4

반응물 2

HCID 55232-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanolHCID 22860073(2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid

생성물 1

HCID 33741Tramadol수율 97.8%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
25 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-bfb169778fad4603a0f1ef7648eeb019
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323368B1

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