Water → 4-methyl-1-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)-1H-imidazole

HRID 273082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 273082
[CH3:1][C:2]1[N:3]=[C:4](S)[N:5]([CH2:7][C:8]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:6]=1.O>C(O)C.[Ni]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:6]=1

Komponenten

5

Edukt 2

HCID 962WaterHCID 178430224HCID 178430224, Verbindung

Produkt 1

HCID 598375014-methyl-1-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)-1H-imidazoleAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

4-methyl-1-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)-1H-imidazole-2-thiol (0.6 g, 1.44 mmol) was dissolved in ethanol (20 mL), water (5 mL) was added, and the mixture was cooled in ice. Raney nickel (4 g) was added, the reaction mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was filtered though Arbocel® and concentrated in vacuo to provide a brown oil. This was purified by flash chromatography on silica gel eluting with ethyl acetate:diethylamine (95:5) to provide the title compound (0.086, 16%) as a clear oil. 1H NMR (400 MHz CDCl3) δ 1.80-1.90 (m, 6H), 2.08-2.18 (m, 7H), 2.65-2.80 (m, 6H), 3.50 (t, 2H), 3.80 (m, 2H), 3.90 (s, 2H), 4.05 (t, 2H), 6.10 (s, 1H), 6.70 (s, 1H), 6.89 (d, 2H), 7.0 (d, 2H). LRMS ESI+ m/z 384 [MH]+.

Aufarbeitung

  1. temperaturethe mixture was cooled in ice
  2. filtrationThe reaction mixture was filtered though Arbocel®
  3. concentrationconcentrated in vacuo
  4. customto provide a brown oil
  5. customThis was purified by flash chromatography on silica gel eluting with ethyl acetate:diethylamine (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-3157723bf48a4b02a834b61c487e1d6d
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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