Reaktion #7177

Reaktionsgleichung

ammonium chloride

N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-ethoxycarbonylmethyloxy-3-methoxyphenylacetamide

intermediate

N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-carboxy-methyloxy-3-methoxyphenylacetamide

sodium borohydride

→

desired compound

Ausbeute 50.2%

N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-(2-hydroxyethyloxy)-3-methoxyphenylacetamide

Ausbeute 50.2%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture is extracted with chloroform
2. 2
   WaschenThe extracted is washed with water
3. 3
   Sonstigethe solvent is evaporated under reduced pressure
4. 4
   SonstigeThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Vorschrift

N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-ethoxycarbonylmethyloxy-3-methoxyphenylacetamide (240 mg), which is an intermediate of Example 72, is dissolved in ethanol, and thereto is added sodium borohydride (35 mg), and the mixture is stirred at room temperature for 2 hours. A saturated aqueous ammonium chloride solution is added thereto, and the mixture is extracted with chloroform. The extracted is washed with water, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (110 mg).

Quelle