Triethylamine → HCID 21186579, Verbindung

HRID 1003612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003612
BrC1(Br)C(=O)C2C(=CC(O[Si](C(C)C)(C(C)C)C(C)C)=C(C)C=2)OC1.[CH3:26][C:27]1[C:28]([Br:51])=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])[O:33][CH2:32][C:31](Br)(Br)[C:30]2=[O:50].[F:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2([OH:65])[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)=[CH:55][CH:54]=1.C(N(CC)CC)C>C(#N)C>[Br:51][C:28]1[C:27]([CH3:26])=[C:36]([O:37][Si:38]([CH:39]([CH3:41])[CH3:40])([CH:42]([CH3:43])[CH3:44])[CH:45]([CH3:47])[CH3:46])[CH:35]=[C:34]2[C:29]=1[C:30](=[O:50])[C:31]([N:62]1[CH2:61][CH2:60][C:59]([C:56]3[CH:57]=[CH:58][C:53]([F:52])=[CH:54][CH:55]=3)([OH:65])[CH2:64][CH2:63]1)=[CH:32][O:33]2

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 774974-(4-Fluorophenyl)piperidin-4-olHCID 21186588HCID 21186588, VerbindungHCID 21186638HCID 21186638, Verbindung

Produkt 1

HCID 21186579HCID 21186579, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3,3-dibromo-6-methyl-7-triisopropylsilyloxychroman-4-one and 6-methyl-3,3,5-tribromo-7-triisopropylsilyloxychroman-4-one (the compounds of Preparation 34, 1.0 g), 4-(4-fluorophenyl)-4-hydroxypiperidine (0.79 g, 4.05 mmol) and triethylamine (0.60 mL, 4.30 mmol) in acetonitrile (30 mL) was stirred 30 min at ambient temperature. The precipitate which formed was collected by filtration to afford 0.188 g of 5-bromo-6-methyl-7-triisopropylsilyloxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one. The filtrate was flash chromatographed on silica gel (1×4 inches packed in hexane) with elution proceeding as follows: 20% ethyl acetate/hexane (100 mL), 0.115 g of 6-methyl -7-triisopropylsilyloxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one as a light yellow solid which had mp 193-195° C.; 20% ethyl acetate/hexane (100 mL) and 40% ethyl acetate/hexane (100 mL), 0.07 g of a mixture; 40% ethyl acetate/hexane (100 mL) and 60% ethyl acetate/hexane (400 mL), 0.30 g of 6-methyl-7-hydroxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one.

Aufarbeitung

  1. customThe precipitate which formed
  2. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e8d388ba44b84355980e51a770b5f8a5
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046213

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