Reacción #7177

Ecuación de reacción

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

Rendimiento 50.2%

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

Rendimiento 50.2%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente