Triethylamine → HCID 54161733、化合物

HRID 2211429ノート

反応式

HRID 2211429 の反応式
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17](Cl)=[O:18].Cl.[C:21]1([C:27]2([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:35][CH:34]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])[C@H:32]3[C@@H:28]2[CH2:29][NH:30][CH2:31]3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:44]1([C:27]2([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:35][CH:34]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])[C@H:32]3[C@@H:28]2[CH2:29][N:30]([C:17](=[O:18])[CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH3:8])[CH2:31]3)[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1795022-(2-Methoxyphenyl)acetyl chlorideHCID 22857049HCID 22857049、化合物

生成物 1

HCID 54161733HCID 54161733、化合物収率 20%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

1.5 cm3 of triethylamine and then 1.6 g of (2-methoxyphenyl)-acetyl chloride are added to a solution of 1.5 g of (3aS,7aR)-4,4-diphenyl-7-(2-methoxyphenyl)-2,3,3a,4,5,7a-hexahydro-isoindole hydrochloride in 20 cm3 of methylene chloride, cooled to 0° C. The mixture is stirred at room temperature for 15 hours; the reaction mixture is washed with twice 40 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 3.6 cm, height 25 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (75/25 by volume) and collecting fractions of 25 cm3. Fractions 14 to 28 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The yellow foam obtained is recrystallised from 10 cm3 of cyclohexane to give 0.38 g of (3aS,7aR)-4,4-diphenyl-2-[(2-methoxyphenyl)-acetyl]-7-(2-methoxyphenyl)-2,3,3a,4,5,7a-hexahydro-isoindole in the form of a beige solid which melts at 142° C.

後処理

  1. washthe reaction mixture is washed with twice 40 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 3.6 cm, height 25 cm)
  5. washby eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (75/25 by volume)
  6. customcollecting fractions of 25 cm3
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe yellow foam obtained
  9. customis recrystallised from 10 cm3 of cyclohexane

出典と根拠

ORDレコード
ord-c245269eed36442a91510dab057d7228
出典データセット
uspto-grants-1995_10
特許番号
US05463077

反応ノート

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