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Lithium borohydride → 2-(6-Bromo-1,8-diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)ethanol

HRID 268653
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 268653
C([O:3][C:4](=O)[CH2:5][C:6]1([CH2:22][CH3:23])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[CH:17][C:16]([Br:19])=[CH:15][C:14]=3[CH2:20][CH3:21])C.[BH4-].[Li+]>O1CCCC1>[Br:19][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([CH2:20][CH3:21])[CH:15]=1)[NH:12][C:11]1[C:6]([CH2:5][CH2:4][OH:3])([CH2:22][CH3:23])[O:7][CH2:8][CH2:9][C:10]2=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 69195683HCID 69195683, Verbindung

Produkt 1

HCID 113370992-(6-Bromo-1,8-diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)ethanolAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (6-bromo-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester (5.2 g, 13.2 mmol) in tetrahydrofuran at room temperature under nitrogen was dropped a 2.0 M solution of lithium borohydride in tetrahydrofuran. The reaction mixture was heated at 90° C. (oil bath) for 5 hours. After cooling to room temperature, it was quenched with 5% hydrochloric acid solution until the excess lithium borohydride was destroyed. Water was added and the mixture extracted with ethyl acetate. Extracts were dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 50% ethyl acetate/hexane) to give the title compound (3.80 g, 82% yield). 1H NMR (CDCl3) δ 8.07 (s, 1H), 7.64 (d, 1H), 7.26 (d, 1H), 4.17 (m, 2H), 3.86 (m, 2H), 2.94 (m, 3H), 2.87 (dt, 1H), 2.76 (t, br, 1H), 2.36 (m, 1H), 2.24 (m, 1H), 2.13 (m, 2H), 1.49 (t, 3H), 1.08 (t, 3H). ES-MS (m/z) 352 [M+1]+, 350 [M−1]−.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customit was quenched with 5% hydrochloric acid solution until the excess lithium borohydride
  3. customwas destroyed
  4. additionWater was added
  5. extractionthe mixture extracted with ethyl acetate
  6. dry with materialExtracts were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica gel, 50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b335506f74a045d7a673bd1811c381bd
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07446122B2

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