Ethanol → tert-Butyl 3-[4-furan-2-yl-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176369
Br[C:2]1[CH:42]=[CH:41][C:5]([CH2:6][O:7][CH:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[CH:16][CH:15]=3)[CH2:12][CH2:11][N:10]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:9]2)=[CH:4][C:3]=1[O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48].[CH2:49](O)[CH3:50].[C:52](=[O:55])([O-])[O-].[Na+].[Na+].[C:58](=O)([O-])O.[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:55]1[CH:52]=[CH:50][CH:49]=[C:58]1[C:2]1[CH:42]=[CH:41][C:5]([CH2:6][O:7][CH:8]2[CH:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[CH:18][CH:19]=3)[CH2:12][CH2:11][N:10]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:9]2)=[CH:4][C:3]=1[O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 68501394Tert-butyl 3-[4-bromo-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Produkt 1

HCID 68505883tert-Butyl 3-[4-furan-2-yl-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

The mixture of 0.500 g of tert-butyl 3-[4-bromo-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 0.023 g of tetrakis(triphenylphosphine)palladium(0) in 6.0 ml of 1,2-dimethoxyethane is stirred at room temperature over 10 minutes, then admixed with 0.114 g of 2-furanboric acid, 0.70 ml of ethanol and 0.68 ml of 2M sodium carbonate solution and stirred at 80° C. over 16 hours. The reaction mixture is cooled, poured onto 1M sodium hydrogencarbonate solution (40 ml) and extracted with tert-butyl methyl ether (2×40 ml). The organic phases are washed successively with water (40 ml) and brine (40 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a brown oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.43 (1:1 EtOAc-heptane); Rt=6.32.

Aufarbeitung

  1. stirringstirred at 80° C. over 16 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with tert-butyl methyl ether (2×40 ml)
  4. washThe organic phases are washed successively with water (40 ml) and brine (40 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-1806d30f2e00481cb38dceb76e671e7e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842688B2

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