N,N,N',N'-Tetramethylethylenediamine → 1',2'-Dihydrospiro[cyclopentane-1,3'-indole]-2'-one

HRID 6995

反応式

HRID 6995 の反応式
[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]

参加物

7

反応物 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 123371,4-DiiodobutaneHCID 321710OxindoleHCID 178418339Butyllithium

生成物 1

HCID 3633431',2'-Dihydrospiro[cyclopentane-1,3'-indole]-2'-one収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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), then the combined organic layers were washed with dil. HCl (pH 1), 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, J=7.5, 1.0 Hz, 1H), 7.14–7.25 (m, 2H), 9.30 (br s, 1H).

後処理

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

出典と根拠

ORDレコード
ord-0951505fdd3d4c26a4e8069af7835193
出典データセット
uspto-grants-2006_08
特許番号
US07084168B2

関連ノート

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