Water → HCID 22025424, Verbindung

HRID 733233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733233
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6](=[O:7])[C:5]2=[CH:15][CH:16]=1.O>CO.[BH4-].[K+]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:6]([OH:7])[N:8]([CH2:11][CH:12]([CH3:13])[CH3:14])[C:9]2=[O:10])=[CH:15][CH:16]=1.[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:15][CH:16]=1)[C:6](=[O:7])[N:8]([CH2:11][CH:12]([CH3:13])[CH3:14])[CH:9]2[OH:10]

Komponenten

6

Edukt 2

HCID 962WaterHCID 4126466HCID 4126466, Verbindung

Produkt 2

HCID 22025424HCID 22025424, VerbindungAusbeute 198,3 %HCID 22025456HCID 22025456, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 4192641Potassium borohydrideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

5-Chloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-chloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are prepared as described in Example 1, starting with 12 g of 4-chloro-N-isobutylphthalimide in 100 cm3 of methanol and 3 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the region of 0° C. and 100 cm3 of distilled water are added dropwise. The methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C. The aqueous phase is extracted twice with 150 cm3 of ethyl acetate. The organic extracts are combined, washed with 50 cm3 of brine, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C. 12 g of 5-chloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-chloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white powder. (Rf=0.15, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (75/25 by volume)).

Aufarbeitung

  1. additionare added dropwise
  2. customThe methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. extractionThe aqueous phase is extracted twice with 150 cm3 of ethyl acetate
  4. washwashed with 50 cm3 of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  8. customThe residue is dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C

Quellen und Nachweise

ORD-Eintrag
ord-695d70673bca483cac65d82da11b8587
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589117B2

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