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

HRID 276990

Reaktionsgleichung

Reaktionsgleichung von HRID 276990
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2fa72be047ef402184968d724e5f9e4b
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355648B1

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