Water → N-Methyl-4-benzyloxy-2-fluoroaniline

HRID 388022

Reaktionsgleichung

Reaktionsgleichung von HRID 388022
N1([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][C:13]=2[F:26])C2C=CC=CC=2N=N1.[BH4-].[Na+].O.C(OCC)(=O)C.O1CCCC1>CN(C)C=O.CO.C(O)C>[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:14][C:13]=1[F:26]

Komponenten

8

Edukt 4

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 21939870Tetrahydrofuran ethyl acetateHCID 22936313N-{1-(1H-Benzotriazolyl)methyl}-4-benzyloxy-2-fluoroaniline

Produkt 1

HCID 22936658N-Methyl-4-benzyloxy-2-fluoroanilineAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

After dissolving N-{1-(1H-benzotriazolyl)methyl}-4-benzyloxy-2-fluoroaniline (14.13 g, 40.56 mmol) in N,N-dimethylformamide (200 ml), methanol (150 ml) and ethanol (50 ml), there was added sodium borohydride (3.06 g, 81.12 mmol) and the mixture was stirred for 2.5 hours at room temperature. There was further added sodium borohydride (0.78 g, 20.28 mmol), and the mixture was stirred for 13.5 hours at room temperature. Water was added to the reaction solution, extraction was performed with ethyl acetate-tetrahydrofuran, the extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate system) to obtain the title compound (5.98 g, 26.31 mmol, 64.87%) as light yellow crystals.

Aufarbeitung

  1. stirringthe mixture was stirred for 13.5 hours at room temperature
  2. washthe extract was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. custompurified by silica gel column chromatography (hexane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-1ce321c63ebf4659ab4778e9a44e8a33
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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