聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → (RS)-2-Phenylsulfanylmethyl-1-aza-bicyclo[2.2.2]octan-3-one

HRID 2356378

反应方程式

HRID 2356378 反应方程式
Cl.[CH2:2]=[C:3]1[C:8](=[O:9])[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2.O.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13]1([S:19][CH2:2][CH:3]2[C:8](=[O:9])[CH:7]3[CH2:10][CH2:11][N:4]2[CH2:5][CH2:6]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参与物

5

反应物 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 7969苯硫酚HCID 184012841-Azabicyclo(2.2.2)octan-3-one, 2-methylene-, hydrochloride (1:1)

产物 1

HCID 11379632(RS)-2-Phenylsulfanylmethyl-1-aza-bicyclo[2.2.2]octan-3-one

试剂、催化剂与溶剂 1

HCID 74236四丁基溴化铵催化剂

反应条件

温度
80 °C

实验过程

To a stirred solution of 2-methylene-3-quinuclidinone hydrochloride (1 g, 0.0057 mol) in water (10 ml) triethylamine (1.73 g, 0.0171 mol), tetra-n-butyl ammonium bromide (180 mg, 0.00057 mol) and thiophenol (0.63 g, 0.0057 mol) were added and the reaction mixture was allowed to stir at 80° C. for 18 h. The completion of reaction was monitored by tlc. The reaction mixture was quenched with ice-cold water (20 ml), extracted with dichloromethane (4×50 ml), organic layers were washed with brine and dried over sodium sulphate, filtered and concentrated to get the crude product which was purified (550 mg) by column chromatography on silica gel using chloroform as eluent.

后处理

  1. customThe completion of reaction
  2. customThe reaction mixture was quenched with ice-cold water (20 ml)
  3. extractionextracted with dichloromethane (4×50 ml), organic layers
  4. washwere washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

来源与证据

ORD记录
ord-9d07993715534551b8d96edf27dfb81b
来源数据集
uspto-grants-2010_07
专利号
US07759361B2

关联笔记

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