N,N,N',N'-四甲基乙二胺 → 1`,2`-二氢螺[环戊烷-1,3`-吲哚]-2`-酮

HRID 276990

反应方程式

HRID 276990 反应方程式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].CN(C)CCN(C)C.ICCCCI>C1COCC1.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[C:2]1=[O:10]

参与物

7

反应物 4

HCID 8037N,N,N',N'-四甲基乙二胺HCID 123371,4-二碘代丁烷HCID 3217102-吲哚酮HCID 178418339正丁基锂

产物 1

HCID 3633431`,2`-二氢螺[环戊烷-1,3`-吲哚]-2`-酮收率 50%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8028四氢呋喃溶剂2 次

实验过程

To a −25° C. solution of oxindole (2.0 g, 15.0 mmol) in 40 (cm3) of anhydrous THF under N2 was added n-butyllithium (1.6 M in hexanes, 19.7 cm3, 31.5 mmol) drop-wise. To the resulting milky solution was added N,N,N′,N′-tetramethylethylenediamine (4.75 cm3, 31.5 mmol). After 30 min. a solution of 1,4-diiodobutane (21.9 g, 70.6 mmol) in THF (3 cm3) was added and the reaction mixture was allowed to warm to RT and stirred for 14 h. The reaction mixture was poured into water, extracted with EtOAc (×2), the combined organic layers were washed with dilute HCl (pH 1) and water (×2), dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:4) to afford the subtitled compound (1.4 g, 7.5 mmol, 50%) as a tan solid: 1H NMR (CDCl3) δ 1.8-2.2 (m, 8H), 6.94 (dd, J=7.5, 1.0 Hz, 1H), 7.01 (dd, J7.5, 1.0 Hz, 1H), 7.14-7.25 (m, 2H), 9.30 (br s, 1H).

后处理

  1. extractionextracted with EtOAc (×2)
  2. washthe combined organic layers were washed with dilute HCl (pH 1) and water (×2)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:4)

来源与证据

ORD记录
ord-2fa72be047ef402184968d724e5f9e4b
来源数据集
uspto-grants-2002_03
专利号
US06355648B1

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