Sodium Hydroxide → {1-[2,4-Bis(trifluoromethyl)benzyl]azetidin-3-yl}methanol

HRID 1620483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620483
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:9][CH:8]([C:10](OC)=[O:11])[CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:7][CH:8]([CH2:10][OH:11])[CH2:9]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86678674Methyl 1-[2,4-bis(trifluoromethyl)benzyl]azetidine-3-carboxylate

Produkt 1

HCID 86678675{1-[2,4-Bis(trifluoromethyl)benzyl]azetidin-3-yl}methanolAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 1-[2,4-bis(trifluoromethyl)benzyl]azetidine-3-carboxylate (341 mg) in THF (5 mL) was added a suspension of lithium aluminum hydride (38 mg) in THF (5 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight. To the reaction mixture was added 1N aqueous sodium hydroxide solution under ice-cooling. The precipitate was removed by filtration, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (180 mg).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-45e20b7672d94fbe8e0a92bc877e7fab
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772277B2

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