Hydrochloric Acid → 6-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile

HRID 1297671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297671
[BH4-].[Li+].C([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]#[N:19])=[C:11]2[CH2:20][CH:21]([CH3:23])[CH3:22])=O)C.Cl>CCOCC.CO.O>[OH:5][CH2:6][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]([C:18]#[N:19])[CH:11]2[CH2:20][CH:21]([CH3:23])[CH3:22]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 58585765HCID 58585765, Verbindung

Produkt 1

HCID 585857716-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrileAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To the suspension of lithium borohydride (93 mg, 4.3 mmol) and methanol (170 uL, 4.3 mmol) in ether (20 mL) was added the solution of 3-cyano-4-isobutyl-quinoline-6-carboxylic acid ethyl ester (example 46d, 600 mg, 2.1 mmol) in ether (5 mL). The mixture was stirred at reflux overnight. The mixture of water and methanol (v/v 1:1, 40 mL) was added to the above solution. Then 1 N HCl (3 mL) was added to quench the reaction. The product was extracted with ethylacetate. The combined organic layers were successively washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 5%-50% ethyl acetate in hexanes in 50 min) afforded 6-hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile (220 mg, 43%) as a yellow solid. LC-MS m/e 243 (MH+).

Aufarbeitung

  1. temperatureat reflux overnight
  2. additionwas added to the above solution
  3. customto quench
  4. customthe reaction
  5. extractionThe product was extracted with ethylacetate
  6. washThe combined organic layers were successively washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d85056dfe1184f62b3f864f720d1d264
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250515B2

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