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Ammonium Chloride → methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-[4-(trifluoromethyl)phenyl]-4-phenyloctahydroisoindole-3a-carboxylate

HRID 324659
ノート
印刷プレビュー

反応式

HRID 324659 の反応式
[Mg].[F:2][C:3]([F:12])([F:11])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.[CH2:13]([N:20]1[CH2:28][C:27]2([C:29]([O:31][CH3:32])=[O:30])[CH:22]([C:23](=[O:39])[CH2:24][CH2:25][CH:26]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>C(OCC)C>[CH2:13]([N:20]1[CH2:28][C:27]2([C:29]([O:31][CH3:32])=[O:30])[CH:22]([C:23]([OH:39])([C:7]3[CH:8]=[CH:9][C:4]([C:3]([F:12])([F:11])[F:2])=[CH:5][CH:6]=3)[CH2:24][CH2:25][CH:26]2[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
参加物反応条件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 25517Ammonium ChlorideHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5462224MagnesiumHCID 11302988methyl(3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate

生成物 1

HCID 86755051methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-[4-(trifluoromethyl)phenyl]-4-phenyloctahydroisoindole-3a-carboxylate収率 66.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
10 °C

実験手順

0.8 g of magnesium turnings was added to a solution of 7.2 g of 4-(trifluoromethyl)bromobenzene in 40 cm3 of dry diethyl ether. The reaction mixture was spontaneously brought to reflux for ten minutes and was then heated at reflux for twenty minutes. The reaction mixture was subsequently cooled and a solution of 5.6 g of methyl (3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate in 40 cm3 of dry diethyl ether was added over fifteen minutes at a temperature in the region of 10° C. The reaction mixture was stirred for ten minutes at a temperature in the region of 10° C. and then poured into 150 cm3 of a saturated aqueous ammonium chloride solution. The aqueous phase was separated by settling and extracted with three times 75 cm3 of diethyl ether. The organic phases were combined, washed successively with three times 75 cm3 of distilled water, dried over magnesium sulphate in the presence of 3S charcoal and concentrated under reduced pressure. After crystallization from 25 cm3 of pentane, 5.2 g of methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-[4-(trifluoromethyl)phenyl]-4-phenyloctahydroisoindole-3a-carboxylate were obtained in the form of a beige solid, the characteristic of which was as follows:

後処理

  1. temperatureto reflux for ten minutes
  2. temperaturewas then heated
  3. temperatureat reflux for twenty minutes
  4. temperatureThe reaction mixture was subsequently cooled
  5. customThe aqueous phase was separated
  6. extractionextracted with three times 75 cm3 of diethyl ether
  7. washwashed successively with three times 75 cm3 of distilled water
  8. dry with materialdried over magnesium sulphate in the presence of 3S charcoal
  9. concentrationconcentrated under reduced pressure
  10. customAfter crystallization from 25 cm3 of pentane

出典と根拠

ORDレコード
ord-c24336ca0a8c4fefa63b03f0a8f5f0a1
出典データセット
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06218406B1

反応ノート

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