Sodium borohydride → 4-[3-(3-Hydroxyisoindolin-1-on-2-yl)propyloxy]pyridine

HRID 964123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 964123
[BH4-].[Na+].[C:3]1(=[O:23])[N:7]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:6](=[O:18])[C:5]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:4]12>C(O)C>[OH:23][CH:3]1[C:4]2[C:5](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:6](=[O:18])[N:7]1[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 190790904-(3-Phthalimidopropyloxy)pyridine

Produkt 1

HCID 190791984-[3-(3-Hydroxyisoindolin-1-on-2-yl)propyloxy]pyridineAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium borohydride [1.89 g (50 mmol)] was added to a solution of 2.82 g (10.0 mmol) of 4-(3-phthalimidopropyloxy)pyridine in 150 ml of ethanol. The mixture was stirred at room temperature for 15 minutes. After the solvent was distilled off, brine was added to the residue. The mixture was extracted with chloroform and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10), and then recrystallized from ethyl acetate to obtain 1.54 g of the desired compound (yield: 54.2%, colorless crystals). mp: 124°-125° C.

Aufarbeitung

  1. distillationAfter the solvent was distilled off
  2. additionbrine was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10)
  7. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-71290fdfe8664aeb9cb57328b3a2545b
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05767121

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