Tetrahydrofuran → N-Carboxy-[1-butyl-4-piperidinylmethyl]-1,2,3,4,4a,9a-hexahydrocarbazole

HRID 1616

Reaktionsgleichung

Reaktionsgleichung von HRID 1616
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11]O)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C[Li].Cl[C:16]([N:18]1[CH:30]2[CH:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:17].C1C[O:34]CC1>>[C:16]([N:18]1[CH:30]2[CH:25]([CH2:26][CH2:27][CH2:28][CH:29]2[CH2:11][CH:8]2[CH2:7][CH2:6][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:10][CH2:9]2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)([OH:34])=[O:17]

Komponenten

5

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 10241250(1-Butylpiperidin-4-yl)methanolHCID 19691851N-chlorocarbonyl-1,2,3,4,4a,9a-hexahydrocarbazoleHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 67817506N-Carboxy-[1-butyl-4-piperidinylmethyl]-1,2,3,4,4a,9a-hexahydrocarbazole

Versuchsvorschrift

1-Butyl-4-piperidinylmethanol (0.500 g 2.12 mmol) was dissolved in dry THF (3 ml) and treated with methyllithium (1.5M solution in diethyl ether) 2.16 ml, 2.33 mmol) with stirring under nitrogen. After 10 minutes, N-chlorocarbonyl-1,2,3,4,4a,9a-hexahydrocarbazole (0.630 g, 2.68 mmol) (Ref: WO 89/09217) in dry THF (5 ml) was added dropwise with stirring. After 48 hours, the reaction mixture was filtered and the filtrate evaporated under reduced pressure. The residue was purified by silica-gel chromatography, eluting with 2% MeOH/CHCl3 -3%MeOH/CHCl3 to give the title compound as a clear, colourless oil, which was converted to the oxalate salt, nap 187°-189° C.

Aufarbeitung

  1. stirringwith stirring
  2. waitAfter 48 hours
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate evaporated under reduced pressure
  5. customThe residue was purified by silica-gel chromatography
  6. washeluting with 2% MeOH/CHCl3 -3%MeOH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-ebab14589329403cb0aad45984b1c528
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726187

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