tert-Butanol → 3-oxo-2-[4-(pyrrolidine-1-carbonyl)benzyl]pentanoic Acid Methyl Ester

HRID 2266603노트

반응식

HRID 2266603 반응식
CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH3:12][O:13][C:14](=[O:20])[CH2:15][C:16](=[O:19])[CH2:17][CH3:18].Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:30])=[CH:25][CH:24]=1>O1CCCC1.O>[CH3:12][O:13][C:14](=[O:20])[CH:15]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:30])=[CH:27][CH:28]=1)[C:16](=[O:19])[CH2:17][CH3:18]

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 121699Methyl 3-oxovalerateHCID 162268621-[4-(Chloromethyl)benzoyl]pyrrolidineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 687803523-oxo-2-[4-(pyrrolidine-1-carbonyl)benzyl]pentanoic Acid Methyl Ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A suspension of potassium tert-butoxide (1.4 g) in anhydrous tetrahydrofuran (40 mL) at 0° C. was treated with a mixture of tert-butanol (1.0 mL) and 3-oxopentanoic acid methyl ester (1.3 mL). The mixture was stirred at 0° C. for 45 minutes and then a solution of (4-chloromethylphenyl)pyrrolidin-1-ylmethanone (2.0 g) in tetrahydrofuran (10 mL) was added and the resulting mixture heated at 70° C. for 24 hours. The mixture was cooled to room temperature, diluted with water and the tetrahydrofuran removed under reduced pressure. The residue was extracted with ethyl acetate and the combined extracts washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (3:7 by volume) to afford title compound, 1.1 g.

후처리

  1. temperaturethe resulting mixture heated at 70° C. for 24 hours
  2. temperatureThe mixture was cooled to room temperature
  3. customthe tetrahydrofuran removed under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe combined extracts washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue purified by column chromatography on silica gel
  9. washeluting with a mixture of ethyl acetate and cyclohexane (3:7 by volume)

출처 및 근거

ORD 기록
ord-953d7b9c7ec74f3189389fe7b6bb39d7
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858640B2

반응 노트

불러오는 중…