Hydrochloric Acid → (R)-1-(1-triisopropylsilylindole-3-yl)-2-propylaminopentane

HRID 1158251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158251
C([Li])(CC)C.Br[C:7]1[N:8]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.[CH2:26]([N:29]1[C@H:33]([CH2:34][CH2:35][CH3:36])[CH2:32]OS1(=O)=O)[CH2:27][CH3:28].Cl>O1CCCC1.C1CCCCC1.CCCCCC>[CH:17]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]([CH2:32][C@H:33]([NH:29][CH2:26][CH2:27][CH3:28])[CH2:34][CH2:35][CH3:36])=[CH:7]1)([CH3:19])[CH3:18]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 674266152-Bromo-1-[tri(propan-2-yl)silyl]-1H-indoleHCID 86630301(R)-3,4-Dipropyl-1,2,3-oxathiazolidine 2,2-dioxideHCID 178418400CID 53628100

Produkt 1

HCID 67426035(R)-1-(1-triisopropylsilylindole-3-yl)-2-propylaminopentaneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 22494920Cyclohexane hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Under an argon atmosphere, s-butyl lithium (a 0.99 mol/L cyclohexane/n-hexane solution, 68.7 mL) was added to a solution of 2-bromo-1-triisopropylsilylindole (11.99 g) in tetrahydrofuran (85 mL) under stirring at −70° C. and then stirred at −70° C. for 30 minutes. A solution of (R)-3,4-dipropyl-1,2,3-oxathiazolidine 2,2-dioxide (7.05 g) in tetrahydrofuran (17 mL) was added to the resulting solution under stirring at −20° C. and then stirred for 13 hours, while the temperature was raised to room temperature. An aqueous 4 mol/L hydrochloric acid solution (34 mL) was added to the solution under water-cooling and stirring, and then vigorously stirred at room temperature for 1 hour. The organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution (30 mL), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to column chromatography (NH-DM1020, from Hexane to AcOEt/Hexane=1/7) and then further purified by column chromatography (NH-DM1020, from AcOEt/Hexane=1/9 to AcOEt/MeOH=9/1) to give (R)-1-(1-triisopropylsilylindole-3-yl)-2-propylaminopentane (9.94 g, 73% yield) as a red oil.

Aufarbeitung

  1. stirringstirred at −70° C. for 30 minutes
  2. stirringunder stirring at −20° C.
  3. stirringstirred for 13 hours, while the temperature
  4. temperaturewas raised to room temperature
  5. temperaturecooling
  6. stirringstirring
  7. stirringvigorously stirred at room temperature for 1 hour
  8. customThe organic layer was separated
  9. washwashed with a saturated aqueous sodium hydrogen carbonate solution (30 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customfurther purified by column chromatography (NH-DM1020, from AcOEt/Hexane=1/9 to AcOEt/MeOH=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-ca742142852b4cac9c5e45bec01b3685
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807840B2

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