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Ethyl Acetate → (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-7-methyl-4,7-perhydroisoindolediol

HRID 55429
ノート
印刷プレビュー

反応式

HRID 55429 の反応式
[OH:1][C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH:10]2[CH:6]([CH2:7][N:8]([C:11](=[O:21])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[CH2:9]2)[C:5](=[O:22])[CH2:4][CH2:3]1.C[Li].[Cl-].[NH4+].[C:35](OCC)(=O)C>C(OCC)C>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:2]1([OH:1])[CH2:3][CH2:4][C:5]([CH3:35])([OH:22])[CH:6]2[CH:10]1[CH2:9][N:8]([C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:7]2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 67714177(3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4-perhydroisoindoloneHCID 178418348HCID 178418348、化合物

生成物 1

HCID 67714344(3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-7-methyl-4,7-perhydroisoindolediol

試薬・触媒・溶媒 1

HCID 3283
Diethyl Ether
溶媒

実験手順

To a suspension, cooled to -70° C. and under an argon atmosphere, of 0.5 g of (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl ]-4-perhydroisoindolone are slowly added 4 cm3 of 1.6 M methyllithium solution in ethyl ether. After returning to room temperature and stirring for 3 hours, the reaction mixture is cooled to +5° C., followed by addition of 25 cm3 of saturated aqueous ammonium chloride solution and 20 cm3 of ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.06-0.20 mm) in ethyl acetate and then in a mixture of ethyl acetate and methanol (90/10 by volume). After drying under reduced pressure and recrystallization in acetonitrile, 0.1 g of (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-7-methyl-4,7-perhydroisoindolediol is obtained, in the form of white crystals melting at 180° C.

後処理

  1. customAfter returning to room temperature
  2. temperaturethe reaction mixture is cooled to +5° C.
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a column of silica gel (particle size 0.06-0.20 mm) in ethyl acetate
  6. additionin a mixture of ethyl acetate and methanol (90/10 by volume)
  7. dry with materialAfter drying under reduced pressure and recrystallization in acetonitrile

出典と根拠

ORDレコード
ord-a0a4d743231c43d0a783e1950f3a64f0
出典データセット
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05624950

反応ノート

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