Benzene → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3,5-dichlorophenyl)ethanol

HRID 1901183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1901183
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[CH:6]=1)[OH:4].O=[C:14]([CH3:28])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:27][O:26][C:24]([CH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH:14]([NH:1][CH2:2][CH:3]([C:5]2[CH:6]=[C:7]([Cl:12])[CH:8]=[C:9]([Cl:11])[CH:10]=2)[OH:4])[CH3:28])=[CH:22][CH:21]=1)=[O:25]

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 37823822-Amino-1-(3,5-dichlorophenyl)ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Produkt 1

HCID 190448372-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3,5-dichlorophenyl)ethanolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Following a procedure similar to that described in Example 3, but using 3.0 g of 2-amino-1-(3,5-dichlorophenyl)ethanol (prepared as described in Preparation 39), 3.87 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 80 ml of benzene, 60 ml of absolute methanol and 2.9 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using ethyl acetate as the eluent, 3.6 g of the title compound were obtained, having an Rf=0.51 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent).

Aufarbeitung

  1. custompurifying the reaction product by column chromatography through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-82cb103cf8714c66aa61f03f4d3513e6
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576340

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