Dichloromethane → 3-(2-Hydroxy-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone

HRID 1087777

Reaktionsgleichung

Reaktionsgleichung von HRID 1087777
[BH4-].[K+].[CH3:3][O:4][C:5]1[N:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([N:15]3[CH:23]([CH2:24][C:25](=[O:31])[CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]3=[O:32])=[N:12]2)=[CH:7][CH:6]=1.ClCCl>O.C(O)C>[OH:31][CH:25]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:24][CH:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:32])[N:15]1[C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[N:14][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[N:12]=1

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 4192641Potassium borohydrideHCID 141821822-(7-Methoxy-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone

Produkt 1

HCID 141821843-(2-Hydroxy-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinoneAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Potassium borohydride (0.41 g) dissolved in distilled water (12 cc) is added at a temperature in the region of 20° C. to a suspension of 2-(7-methoxy-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone (3.0 g) in ethanol (50 cc), and the suspension is stirred for 16 hours at a temperature in the region of 20° C. The reaction mixture is then poured into a mixture of distilled water (300 cc) and dichloromethane (150 cc) which has been cooled to a temperature in the region of 0° C. The aqueous phase is separated after settling has occurred, and re-extracted with dichloromethane (2×150 cc). The organic phases are combined, washed with distilled water (3×25 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The product obtained is recrystallized twice in diisopropyl ether. 3-(2-Hydroxy-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (2.0 g), m.p. 110° C., is thereby obtained.

Aufarbeitung

  1. temperaturehas been cooled to a temperature in the region of 0° C
  2. customThe aqueous phase is separated after settling
  3. extractionre-extracted with dichloromethane (2×150 cc)
  4. washwashed with distilled water (3×25 cc)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  8. customThe product obtained
  9. customis recrystallized twice in diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c263b349e8e94a5d901bb0826105edb9
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04960779

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