2-Amino-1-(3-fluorophenyl)ethan-1-ol → N-{2-(4-{(E)-2-Carbomethoxyethenyl}phenyl)-1-methylethyl}-2-hydroxy-2-(3-fluorophenyl) ethanamine

HRID 1105624

Reaktionsgleichung

Reaktionsgleichung von HRID 1105624
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1)[CH2:3][NH2:4].[C:12](/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](=O)[CH3:26])=[CH:20][CH:19]=1)([O:14][CH3:15])=[O:13]>>[C:12](/[CH:16]=[CH:17]/[C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH:25]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=2)[CH3:26])=[CH:22][CH:23]=1)([O:14][CH3:15])=[O:13]

Komponenten

3

Edukt 2

HCID 358002-Amino-1-(3-fluorophenyl)ethan-1-olHCID 198745324-{(E)-2-carbomethoxyethenyl}phenylpropan-2-one

Produkt 1

HCID 70529992N-{2-(4-{(E)-2-Carbomethoxyethenyl}phenyl)-1-methylethyl}-2-hydroxy-2-(3-fluorophenyl) ethanamineAusbeute 39,2 %

Versuchsvorschrift

This was prepared in an identical manner to the compound described in Example 1 using 2-hydroxy-2-(3-fluorophenyl) ethanamine (1.55 g) and 4{(E)-2-carbomethoxyethenyl}phenylpropan-2-one (2.18 g). Elution with 1% methanolchloroform on Kieselgel 60 gave the title compound (1.4 g) m.p. 75°-110° C. (benzene-heptane) as an ~45:55 mixture of diastereoisomers. τ(CDCl3) 8.9 (3H, d, J=6 Hz), 6.9-7.8 (7H, m, 2H disappears with D2O), 6.25 (3H, s), 5.45 (1H, m), 3.6 (1H, d, J=16 Hz), 2.55-3.2 (8H, m), 2.35 (1H, d, J=16 Hz).

Aufarbeitung

  1. customThis was prepared in an identical manner to the compound
  2. washElution with 1% methanolchloroform on Kieselgel 60

Quellen und Nachweise

ORD-Eintrag
ord-6b6f18a4605b4236b5968c98a05f84fb
Quelldatensatz
uspto-grants-1982_01
Patentnummer
US04309443

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