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

HRID 1433680

Reaktionsgleichung

Reaktionsgleichung von HRID 1433680
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 brine 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 brine
  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-23425df8c8ec4f1f93c19d4789828845
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612092B2

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