L-Methionine → (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methoxypropyl)-phenol

HRID 1631842노트

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HRID 1631842 반응식
Cl.C[O:3][C:4]1[CH:5]=[C:6]([C@H:10]([CH2:17][CH3:18])[C@@H:11](C)[CH2:12][N:13]([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1.N[C@H]([C:25](O)=[O:26])CCSC>CS(O)(=O)=O>[CH3:14][N:13]([CH3:15])[CH2:12][C@H:11]([O:26][CH3:25])[C@@H:10]([C:6]1[CH:5]=[C:4]([OH:3])[CH:9]=[CH:8][CH:7]=1)[CH2:17][CH3:18]

참가 물질

4

반응물 2

HCID 6137L-MethionineHCID 247860813(3-Methoxyphenyl)-N,N,2-trimethyl pentane-1-amine hydrochloride, (2R,3R)-

생성물 1

HCID 86690044(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methoxypropyl)-phenol수율 105.3%

시약·촉매·용매 1

HCID 6395Methanesulfonic Acid용매

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온도
77.5 °C

실험 절차

In 28 mL of methanesulfonic acid, (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentan-1-amine HCl (6.0 g, 0.022 moles) is dissolved, and methionine (4.7 g, 0.031 moles) is added to the solution. The reaction is stirred at the temperature of 75-80° C. for 16-20 hours. It is then cooled to 15-25° C. and the following is added: purified water (20 mL), slowly at this temperature. The pH is brought to the value of 10-11 by means of the addition of 28% NaOH (about 35 mL), maintaining the temperature below 50° C. Then, ethyl acetate (30 mL) is added to the mixture. The mixture is then stirred for 30 minutes and the organic phase is separated. The organic phase, with dark color, is filtered over a silica panel and washed with 30 mL of ethyl acetate. A yellowish transparent solution is obtained. The solvent is removed under vacuum, obtaining about 5.5 g of oil which, left at ambient temperature, solidifies.

후처리

  1. temperatureIt is then cooled to 15-25° C.
  2. additionthe following is added
  3. custompurified water (20 mL)
  4. additionThe pH is brought to the value of 10-11 by means of the addition of 28% NaOH (about 35 mL)
  5. temperaturemaintaining the temperature below 50° C
  6. additionThen, ethyl acetate (30 mL) is added to the mixture
  7. stirringThe mixture is then stirred for 30 minutes
  8. customthe organic phase is separated
  9. filtrationThe organic phase, with dark color, is filtered over a silica panel
  10. washwashed with 30 mL of ethyl acetate
  11. customA yellowish transparent solution is obtained
  12. customThe solvent is removed under vacuum

출처 및 근거

ORD 기록
ord-6512ab6cb2264bd6bd1fe08786a0ec29
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791287B2

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