Triethylamine → (3aRS,7aRS)-7,7-diphenyl-2-[2-(2-pyridyl)acetyl]-4-perhydroisoindolone

HRID 1029913

반응식

HRID 1029913 반응식
C(N(CC)CC)C.Cl.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=O.Cl.[C:20]1([C:26]2([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:34]3[CH:30]([CH2:31][NH:32][CH2:33]3)[C:29](=[O:35])[CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:36]1([C:26]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:34]3[CH:30]([CH2:31][N:32]([C:16](=[O:18])[CH2:15][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=4)[CH2:33]3)[C:29](=[O:35])[CH2:28][CH2:27]2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

생성물 1

HCID 67915946(3aRS,7aRS)-7,7-diphenyl-2-[2-(2-pyridyl)acetyl]-4-perhydroisoindolone수율 39.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Triethylamine (1.4 cc) is added to a suspension of 2-(2-pyridyl)acetic acid hydrochloride (1.73 g) in dry dichloromethane (30 cc). The solution is cooled to +5° C. and then treated with N,N'-carbonyldiimidazole (1.62 g). The mixture is stirred for 15 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (3.27 g) and triethylamine (2.8 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred at 20° C. for 2 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in a mixture of ethyl acetate (100 cc) and water (75 cc). The organic phase is washed with water (50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from a mixture of acetonitrile (30 cc) and isopropyl ether (30 cc). (3aRS,7aRS)-7,7-diphenyl-2-[2-(2-pyridyl)acetyl]-4-perhydroisoindolone (1.6 g) is obtained in the form of white crystals melting at 195° C.

후처리

  1. temperatureThe solution is cooled to +5° C.
  2. stirringThe reaction mixture is stirred at 20° C. for 2 hours
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. additionThe residue is taken up in a mixture of ethyl acetate (100 cc) and water (75 cc)
  5. washThe organic phase is washed with water (50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  9. customThe residue is recrystallized from a mixture of acetonitrile (30 cc) and isopropyl ether (30 cc)

출처 및 근거

ORD 기록
ord-8adcab339b624732a00d0f3c5f921b4b
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102667

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