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

HRID 1029913

反応式

HRID 1029913 の反応式
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

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8adcab339b624732a00d0f3c5f921b4b
出典データセット
uspto-grants-1992_04
特許番号
US05102667

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