4-Methylmorpholine → [4-(Morpholin-4-yl)phenyl]methanol

HRID 49832

Reaktionsgleichung

Reaktionsgleichung von HRID 49832
[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O.CC(O)=O.CO>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:14][CH:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

9

Edukt 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 3452784-(Morpholin-4-yl)benzoic acidHCID 4311764Sodium borohydride

Produkt 1

HCID 2776456[4-(Morpholin-4-yl)phenyl]methanolAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-(4-morpholinyl)benzoic acid (1.00 g, 4.83 mmol) and 4-methylmorpholine (0.53 mL, 4.8 mmol) in tetrahydrofuran (25 mL) at −10° C. was treated with ethyl chloroformate (0.46 mL, 4.8 mmol). After 0.25 h, the mixture was treated with sodium borohydride (550 mg, 14.5 mmol) followed by MeOH (50 mL) slowly. The mixture was then treated with 5% HOAc in water and the mixture was concentrated. The residue was purified by chromatography (SiO2, EtOAc:hexanes) yielding 164 mg (18%) of the title compound.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by chromatography (SiO2, EtOAc:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5fc4285abbbc4150bb295b67846ad02a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710057B2

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