Diethyl Ether → {4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine

HRID 1633672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633672
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].CCOCC.[OH-].[Na+]>C(O)(C(F)(F)F)=O.O>[NH3:8].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 18679470{4-[1-(4-Bromo-phenyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine

Produkt 2

HCID 222AmmoniaHCID 18679539{4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amineAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

104 mg (0.25 mmol) {4-[1-(4-Bromo-phenyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine in 1 ml TFA were treated with 32 mg (0.5 mmol) NaCNBH3 at 0° C. for 5 min and 30 min at RT. Ether and water were added, followed by 2M NaOH. The inorganic phase was extracted with ether, the combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1-1%sat.NH3 in MeOH yielded 40 mg (38%) {4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine as light yellow waxy solid, MS: 417 (MH+, 1Br).

Aufarbeitung

  1. extractionThe inorganic phase was extracted with ether
  2. washthe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-3f986c99150c4aa2a40db74674222a8b
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

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