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

HRID 1631842ノート

反応式

HRID 1631842 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒

反応条件

温度
77.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6512ab6cb2264bd6bd1fe08786a0ec29
出典データセット
uspto-grants-2014_07
特許番号
US08791287B2

反応ノート

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