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

HRID 9318

반응식

HRID 9318 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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, J=7.5, 1.0 Hz, 1H), 7.14–7.25 (m, 2H), 9.30 (br s, 1H).

후처리

  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)

출처 및 근거

ORD 기록
ord-70fbe5d426504ba9b0472297ac3af260
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091234B2

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