Potassium Carbonate → tert-Butyl 4-(4-{2-[2-(2-methoxyphenyl)ethoxy]ethoxy}phenyl)-3-[1-(3-methoxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethoxy]piperidine-1-carboxylate

HRID 1176287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176287
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]2[O:21][CH2:22][C:23]2[CH:32]=[C:31]3[C:26]([CH2:27][CH2:28][C:29](=[O:38])[N:30]3[CH2:33][CH2:34][CH2:35][O:36][CH3:37])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O[CH2:49][CH2:50][O:51][CH2:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[O:60][CH3:61])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:61][O:60][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=1[CH2:53][CH2:52][O:51][CH2:50][CH2:49][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:10][CH:9]2[O:21][CH2:22][C:23]2[CH:32]=[C:31]3[C:26]([CH2:27][CH2:28][C:29](=[O:38])[N:30]3[CH2:33][CH2:34][CH2:35][O:36][CH3:37])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 68501561Tert-butyl 4-(4-hydroxyphenyl)-3-[1-(3-methoxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethoxy]piperidine-1-carboxylateHCID 866099992-[2-(2-Methoxyphenyl)ethoxy]ethyl toluene-4-sulphonate

Produkt 1

HCID 68500681tert-Butyl 4-(4-{2-[2-(2-methoxyphenyl)ethoxy]ethoxy}phenyl)-3-[1-(3-methoxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethoxy]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The mixture of 0.133 g of tert-butyl 4-(4-hydroxyphenyl)-3-[1-(3-methoxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethoxy]piperidine-1-carboxylate (Example 44d), 0.106 g of 2-[2-(2-methoxyphenyl)ethoxy]ethyl toluene-4-sulphonate and 0.173 g of potassium carbonate in 2.5 ml of N,N-dimethylformamide is stirred at 60° C. for 20 hours. The reaction mixture is subsequently cooled, poured onto water (25 ml) and extracted with tert-butyl methyl ether (2×25 ml). The organic phases are washed with brine (25 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (2:1 EtOAc-heptane); Rt=5.87.

Aufarbeitung

  1. temperatureThe reaction mixture is subsequently cooled
  2. additionpoured onto water (25 ml)
  3. extractionextracted with tert-butyl methyl ether (2×25 ml)
  4. washThe organic phases are washed with brine (25 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-5076866e595943bdbb22e6045ed56082
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842688B2

Notizen zur Reaktion

Wird geladen…