Tetrabutylammonium Fluoride → Benzyl 3-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-7-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1712517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712517
[CH3:1][C:2]1([CH3:58])[C:10]2[C:5](=[C:6]([CH2:11][O:12][CH:13]3[CH:18]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[O:37][CH3:38])=[CH:21][CH:20]=4)[CH2:17][CH2:16][N:15]([C:39]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[O:40])[CH2:14]3)[CH:7]=[CH:8][CH:9]=2)[N:4](COCC[Si](C)(C)C)[C:3]1=[O:57].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C:2]1([CH3:58])[C:10]2[C:5](=[C:6]([CH2:11][O:12][CH:13]3[CH:18]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[O:37][CH3:38])=[CH:23][CH:24]=4)[CH2:17][CH2:16][N:15]([C:39]([O:41][CH2:42][C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[O:40])[CH2:14]3)[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:57]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 68504422benzyl 3-[3,3-dimethyl-2-oxo-1-(2-trimethylsilanylethoxymethyl)-2,3-dihydro-1H-indol-7-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Produkt 1

HCID 68498981Benzyl 3-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-7-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The solution of 0.690 g of benzyl 3-[3,3-dimethyl-2-oxo-1-(2-trimethylsilanylethoxymethyl)-2,3-dihydro-1H-indol-7-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 7.2 ml of tetrahydrofuran is admixed with 17.9 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran) and stirred at reflux over 26 hours. The reaction mixture is cooled, poured onto water (100 ml) and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed with brine (1×100 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.22 (1:1 EtOAc-heptane); Rt=5.89.

Aufarbeitung

  1. temperatureat reflux over 26 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water (100 ml)
  4. extractionextracted with tert-butyl methyl ether (2×100 ml)
  5. washThe organic phases are washed with brine (1×100 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-1a76f7349d9f4260afacd13fec6a7f58
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790715B2

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