Sodium hydride → tert-Butyl 3-{2-[3-(2-acetylaminoethyl)indol-1-yl]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176335

Reaktionsgleichung

Reaktionsgleichung von HRID 1176335
[CH3:1][O:2][C:3]1[CH:47]=[CH:46][CH:45]=[CH:44][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][CH2:32]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:13][CH:12]=1.[NH:48]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:50]([CH2:57][CH2:58][NH:59][C:60](=[O:62])[CH3:61])=[CH:49]1.[H-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:60]([NH:59][CH2:58][CH2:57][C:50]1[C:51]2[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:48]([CH2:32][CH2:31][O:30][CH:18]2[CH:17]([C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]4[CH:44]=[CH:45][CH:46]=[CH:47][C:3]=4[O:2][CH3:1])=[CH:16][CH:15]=3)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19]2)[CH:49]=1)(=[O:62])[CH3:61]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 70547N-AcetyltryptamineHCID 516892Sodium BicarbonateHCID 86609984Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate

Produkt 1

HCID 68501498tert-Butyl 3-{2-[3-(2-acetylaminoethyl)indol-1-yl]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 0.20 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate (Example 14b) and 0.067 g of N-[2-(1H-indol-3-yl)ethyl]acetamide in 7 ml of N,N-dimethylformamide is admixed at 0° C. with 0.024 g of sodium hydride dispersion (60%) and stirred at room temperature over 20 hours. The reaction mixture is poured onto saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.35 (EtOAc); Rt=5.69.

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0fb41553436545509cd2e817fed0846f
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842688B2

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