Sodium hydride → Benzyl 4-{4-[2-(2,5-difluorophenoxy)ethoxymethyl]phenyl}-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

HRID 1176589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176589
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH:10]2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]3[O:35][CH2:34][CH2:33][N:32]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:31]=3[CH:41]=2)=[CH:5][CH:4]=1.[F:42][C:43]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:44]=1[O:45][CH2:46][CH2:47][OH:48].[H-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[F:42][C:43]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:44]=1[O:45][CH2:46][CH2:47][O:48][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH:10]2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]3[O:35][CH2:34][CH2:33][N:32]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:31]=3[CH:41]=2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 632691512-(2,5-Difluoro-phenoxy)-ethanolHCID 68501265HCID 68501265, Verbindung

Produkt 1

HCID 68500617Benzyl 4-{4-[2-(2,5-difluorophenoxy)ethoxymethyl]phenyl}-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The stirred solution of 0.150 g of benzyl 4-(4-chloromethylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate, 0.035 g of 2-(2,5-difluorophenoxy)ethanol and 2.0 ml of N,N-dimethylformamide is admixed at 0° C. with 0.0094 g of sodium hydride dispersion (55%). The reaction mixture is stirred at room temperature over a further 1 hour and subsequently poured onto 1M sodium hydrogencarbonate solution (30 ml). The mixture is extracted with tert-butyl methyl ether (2×30 ml). The organic phases are washed successively with water (30 ml) and brine (30 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.33 (1:1 EtOAc-heptane); Rt=5.78.

Aufarbeitung

  1. extractionThe mixture is extracted with tert-butyl methyl ether (2×30 ml)
  2. washThe organic phases are washed successively with water (30 ml) and brine (30 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-721890691500432299ca1793dfefa8ca
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842688B2

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