海萝胶 → 3-Ethenyl-3-hydroxy-1-azabicyclo[2.2.2]octane

HRID 49601

反应方程式

HRID 49601 反应方程式
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.[CH:10]([Mg]Br)=[CH2:11].Cl.[OH-].[Na+]>O1CCCC1>[CH:10]([C:3]1([OH:9])[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)=[CH2:11]

参与物

6

反应物 4

HCID 313海萝胶HCID 14798二甲基对苯二胺二盐酸HCID 195073-奎宁环酮HCID 178418507HCID 178418507，化合物

产物 1

HCID 226207783-Ethenyl-3-hydroxy-1-azabicyclo[2.2.2]octane收率 54%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

实验过程

Under an argon atmosphere, a solution of 3-quinuclidinone (1.25 g, 10 mmol) in anhydrous tetrahydrofuran (10 mL) was added over 15 minutes to a 1 M solution of vinylmagnesium bromide in tetrahydrofuran (20 mL, 20 mmol) at 0° C. to 5° C., stirred at room temperature for 24 hours, cooled to 0° C., and acidified to pH 1 with 6 M hydrochloric acid. The mixture was stirred for 15 minutes, basified to pH 10 with 25% aqueous sodium hydroxide, extracted with chloroform (4×50 mL) and chloroform/methanol (4:1, 50 mL), combined the organic layers, dried (MgSO4), evaporated under reduced pressure and purified by flash chromatography (eluting with ammoniated chloroform/methanol, 85:15) to obtain the title compound (830 mg, 5.4 mmol, 54%).

后处理

  1. temperaturecooled to 0° C.
  2. stirringThe mixture was stirred for 15 minutes
  3. extractionextracted with chloroform (4×50 mL) and chloroform/methanol (4:1, 50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. custompurified by flash chromatography (eluting with ammoniated chloroform/methanol, 85:15)

来源与证据

ORD记录
ord-104634446aeb42d7ba0c56844f5c4ea7
来源数据集
uspto-grants-2004_03
专利号
US06706878B2

关联笔记

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