Reaction #7177

Reaction equation

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

Yield 50.2%

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

Yield 50.2%

Solvents

ethanol

Conditions

Workup

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

Procedure

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).

Source