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2-Methoxyphenylacetic acid → (3aRS,7SR,7aRS)-7-methyl-7-phenyl-2-[(2methoxyphenyl)acetyl]-4-perhydroisoindolone

HRID 55415
ノート
印刷プレビュー

反応式

HRID 55415 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.Cl.[CH3:14][C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]2[CH:19]([CH2:20][NH:21][CH2:22]2)[C:18](=[O:24])[CH2:17][CH2:16]1.C(N(CC)CC)C>ClCCl>[CH3:14][C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]2[CH:19]([CH2:20][N:21]([C:10](=[O:12])[CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:22]2)[C:18](=[O:24])[CH2:17][CH2:16]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 71342-Methoxyphenylacetic acidHCID 8471TriethylamineHCID 67713963(3aRS,7SR,7aRS)-7-methyl-7-phenyl-4-perhydroisoindolone hydrochloride

生成物 1

HCID 67714033(3aRS,7SR,7aRS)-7-methyl-7-phenyl-2-[(2methoxyphenyl)acetyl]-4-perhydroisoindolone収率 49.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 1.66 g of 2-methoxyphenylacetic acid in 40 cm3 of dichloromethane are added, at 4° C., 1.62 g of N,N'-carbonyldiimidazole. Stirring for 30 minutes at room temperature is followed by dropwise addition of a solution containing 1.85 g of (3aRS,7SR,7aRS)-7-methyl-7-phenyl-4-perhydroisoindolone hydrochloride and 0.7 g of triethylamine in 30 cm3 of dichloromethane. After stirring for 2 hours, the reaction mixture is washed twice with 50 cm3 of water and then with 50 cm3 of saturated aqueous sodium chloride solution. The organic phase is separated out after settling has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 3 cm, height 15 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (80/20 by volume) and collecting 50 cm3 fractions. Fractions 16 to 60 are combined and then concentrated to dryness under reduced pressure (2.5 kPa). The residue is crystallized in 30 cm3 of ethyl acetate. 1.3 g of (3aRS,7SR,7aRS)-7-methyl-7-phenyl-2-[(2-methoxyphenyl)acetyl]-4-perhydroisoindolone are obtained, in the form of white crystals melting at 160° C.

後処理

  1. additionis followed by dropwise addition of a solution
  2. stirringAfter stirring for 2 hours
  3. washthe reaction mixture is washed twice with 50 cm3 of water
  4. customThe organic phase is separated out after settling
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 3 cm, height 15 cm)
  9. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (80/20 by volume)
  10. customcollecting 50 cm3 fractions
  11. concentrationconcentrated to dryness under reduced pressure (2.5 kPa)
  12. customThe residue is crystallized in 30 cm3 of ethyl acetate

出典と根拠

ORDレコード
ord-758961b7be7d45b5a4c2c263c57f103b
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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