Water → N-[2-(4-(3-Carbomethoxyprop-2-eneoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(4-chlorophenyl) ethanamine

HRID 1758978

Reaktionsgleichung

[C:1]([CH:5]=[CH:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](=O)[CH3:17])=[CH:11][CH:10]=1)([O:3][CH3:4])=[O:2].[OH:19][CH:20]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH2:21][NH2:22].O>C1C=CC=CC=1>[C:1]([CH:5]=[CH:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:22][CH2:21][CH:20]([OH:19])[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH3:17])=[CH:11][CH:10]=1)([O:3][CH3:4])=[O:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A mixture of 1-(4-(3-carbomethoxyprop-2-eneoxy) phenyl) propan-2-one (2.27 g) and 2-hydroxy-2-(4-chlorophenyl) ethanamine (1.57 g) in benzene (100 ml) was boiled under reflux with azeotropic removal of water using a Dean and Stark trap. The solution was evaporated, the residue dissolved in methanol (50 ml), cooled in ice and sodium borohydride added. The solution was stirred for 1 hour at 0° C., the methanol evaporated, and the residue partitioned between water and ethyl acetate. The ethyl acetate layer was dried (MgSO4) and evaporated to give a cream solid (3.1 g) which was crystallised from ethyl acetate m.p. 120°-122°. as a 0:100 mixture of diastereoisomers. Recrystallisation of the mother liquors from hexane gave a 70:30 mixture of diastereoisomers, m.p. 55°-65°.

Aufarbeitung

customThe solution was evaporated
dissolutionthe residue dissolved in methanol (50 ml)
temperaturecooled in ice
additionsodium borohydride added
customthe methanol evaporated
customthe residue partitioned between water and ethyl acetate
dry with materialThe ethyl acetate layer was dried (MgSO4)
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-6fafafae0c994d71975a9d13a33527df
Quelldatensatz: uspto-grants-1982_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04338333

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