Methyl p-toluenesulfonate → N-[1-(S)-[alpha-(R)-methoxybenzyl)-3-methyl-butyl]phthalimide

HRID 1935422노트

반응식

HRID 1935422 반응식
[OH:1][C@@H:2]([C@@H:9]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH2:10][CH:11]([CH3:13])[CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:25]1(C)C=CC(S(OC)(=O)=O)=CC=1.[H-].[Na+]>C1(C)C=CC=CC=1>[CH3:25][O:1][C@@H:2]([C@@H:9]([N:14]1[C:15](=[O:24])[C:16]2=[CH:23][CH:22]=[CH:21][CH:20]=[C:17]2[C:18]1=[O:19])[CH2:10][CH:11]([CH3:13])[CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 12087153N-[1-(S)-[alpha-(R)-hydroxybenzyl]-3-methylbutyl]phthalimide

생성물 1

HCID 18741230N-[1-(S)-[alpha-(R)-methoxybenzyl)-3-methyl-butyl]phthalimide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of N-[1-(S)-[α-(R)-hydroxybenzyl]-3-methylbutyl]phthalimide (30.4 g, 94.0 mmol.) in toluene (380 mL) were successively added methyl p-toluenesulfonate (19.2 g, 103 mmol.) and 60% sodium hydride (4.13 g, 103 mmol.). The resulting mixture was heated under reflux for 18 hours under stirring, cooled to room temperature, successively washed with water and aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by middle pressure column chromatography (n-hexane/ethyl acetate=5/1), to give N-[1-(S)-[α-(R)-methoxybenzyl]-3-methylbutyl]phthalimide as a white crystalline product (25.6 g, yield: 81%).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 18 hours
  3. washsuccessively washed with water and aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by middle pressure column chromatography (n-hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-db7dc8ea1cbe4d0b9401ea7af0ffc30e
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06387908B1

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