Sodium borohydride → 4-[3-(2-Hydroxymethylbenzoyl)aminopropyloxy]pyridine

HRID 274693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274693
[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][CH2:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)=[O:18]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 190791834-[3-(2-Hydroxymethylbenzoyl)aminopropyloxy]pyridineAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium borohydride [3.78 g (100 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 3 hours. After the solvent was distilled off, brine was added to the residue. The mixture was extracted with chloroform and dried over anhydrous magnesium sulfate. The solvent was distilled off and then the residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10) to obtain 1.488 g of the desired compound (yield: 52.0% colorless crystals).

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)

Quellen und Nachweise

ORD-Eintrag
ord-e008ab71ebd147ad9978b80a46d41c1c
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389658

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