Water → Bis(tropan-3-yl) succinate

HRID 650612

反応式

HRID 650612 の反応式
[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([OH:10])[CH2:9][CH:3]1[CH2:4][CH2:5]2.[C:11](Cl)(=[O:17])[CH2:12][CH2:13][C:14](Cl)=[O:15].[OH2:19].[OH-].[Na+]>C(Cl)Cl>[C:11]([O:17][CH:8]1[CH2:7][C@H:6]2[N:2]([CH3:1])[C@H:3]([CH2:4][CH2:5]2)[CH2:9]1)(=[O:19])[CH2:12][CH2:13][C:14]([O:10][CH:8]1[CH2:9][C@H:3]2[N:2]([CH3:1])[C@H:6]([CH2:5][CH2:4]2)[CH2:7]1)=[O:15]

参加物

6

反応物 4

HCID 962WaterHCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 10970Succinyl chlorideHCID 14798Sodium Hydroxide

生成物 1

HCID 11824654Bis(tropan-3-yl) succinate収率 65%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 14.1 g (100 mmol) of tropine in 50 mL of methylene chloride is added dropwise 7.75 g (50 mmol) of succinyl chloride in 100 mL of methylene chloride with cooling in an ice bath. Then the mixture is allowed to warm to room temperature. After the reaction mixture is poured into 200 mL of cold water, the aqueous layer is adjusted to pH 10-11 with 6 N NaOH aqueous solution and extracted with chloroform. The resulting oil is purified by column chromatography (silica gel, 20% methanol in chloroform) to yield 11.8 g (65%) of bis-tropan-3-yl succinate as a thick oil.

後処理

  1. temperaturewith cooling in an ice bath
  2. extractionextracted with chloroform
  3. customThe resulting oil is purified by column chromatography (silica gel, 20% methanol in chloroform)

出典と根拠

ORDレコード
ord-45c38c573f15441f8d69561738e12d25
出典データセット
uspto-grants-2001_08
特許番号
US06274623B1

関連ノート

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