Benzene → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol

HRID 1682720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1682720
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)[OH:4].O=[C:21]([CH3:35])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:34][O:33][C:31]([CH2:30][C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH:21]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=2)[OH:4])[CH3:35])=[CH:29][CH:28]=1)=[O:32]

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 5003444Sodium cyanoborohydrideHCID 218321632-Amino-1-(3,5-di-t-butyl-4-hydroxyphenyl)ethanolHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Produkt 1

HCID 218321892-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3,5-di-t-butyl-4-hydroxyphenyl)ethanolAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A procedure similar to that described in Example 6 was repeated, except that 3 g of 2-amino-1-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol (prepared as described in Preparation 35), 2.2 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 100 ml of benzene, 60 ml of absolute methanol and 4 g of sodium cyanoborohydride were used, and that the product was purified by repeated column chromatography through silica gel, using as the eluent first ethyl acetate and then a 1:1 by volume mixture of benzene and ethyl acetate. 2.1 g of 2-[2-(4-methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3,5-di-t-butyl-4hydroxyphenyl)ethanol were obtained. This product was then mixed with 246 mg of fumaric acid, and the mixture was recrystallized from ethyl acetate, to give 1.5 g of the title compound as crystals, melting at 171°-174° C.

Aufarbeitung

  1. customthat the product was purified
  2. additiona 1:1 by volume mixture of benzene and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c0434956589f4b19b1168fc9a9f73fd9
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05635534

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