Carbon Dioxide → 1-Butylisoquinoline-7-carboxylic acid

HRID 14266

Reaktionsgleichung

Reaktionsgleichung von HRID 14266
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.C([Li])(CC)C.[C:21](=[O:23])=[O:22]>C(OCC)C>[CH2:12]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:21]([OH:23])=[O:22])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)[CH2:13][CH2:14][CH3:15]

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 210859957-Bromo-1-butylisoquinolineHCID 178418400CID 53628100

Produkt 1

HCID 210851771-Butylisoquinoline-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a −60° C. solution of 7-bromo-1-butylisoquinoline prepared in step 1 (940 mg, 3.55 mmol) in diethyl ether (15 mL) was added sec-butyl lithium (3.0 nL, 1.3 M cyclohexanes, 3.90 mmol) to yield a dark green solution. The reaction mixture was stirred at −60° C. for an additional 15 minutes at which time carbon dioxide gas was bubbled through the solution for 20 minutes with the aid of a gas dispersion tube. The resulting solution was then allowed to warm to room temperature and concentrated under reduced pressure to yield a pink solid. The residue was partitioned between ethyl acetate and water and then acidified to pH 7 with 1 N hydrochloric acid. The aqueous phase was extracted again with ethyl acetate and the combined organic phases were washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated to yield 1-butylisoquinoline-7-carboxylic acid (299 mg). ESI MS m/z 230 [M+H]+.

Aufarbeitung

  1. customto yield a dark green solution
  2. customwas bubbled through the solution for 20 minutes with the aid of a gas dispersion tube
  3. concentrationconcentrated under reduced pressure
  4. customto yield a pink solid
  5. customThe residue was partitioned between ethyl acetate and water
  6. extractionThe aqueous phase was extracted again with ethyl acetate
  7. washthe combined organic phases were washed with saturated sodium chloride
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6505ba6f80fd43c181e2c4f91ee33502
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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