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Issue 20, 1999
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Regioselective alkylation of phenol with cyclopentanol over montmorillonite K10: An efficient synthesis of 1-(2-cyclopentylphenoxy)-3-[(1,1-dimethylethyl)amino]propan-2-ol {(S )-penbutolol}

Abstract

Regioselective alkylation of phenol with cyclopentanol is achieved over Montmorillonite K10 clay, producing 2-cyclopentylphenol, the key intermediate. The synthesis of optically active (S )-penbutolol 1, an important antihypertensive drug, is realized in 5 steps from 2-cyclopentylphenol by employing Sharpless asymmetric dihydroxylation.

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Article type: Paper
DOI: 10.1039/A902479D
J. Chem. Soc., Perkin Trans. 1, 1999, 3015-3018

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    Regioselective alkylation of phenol with cyclopentanol over montmorillonite K10: An efficient synthesis of 1-(2-cyclopentylphenoxy)-3-[(1,1-dimethylethyl)amino]propan-2-ol {(S )-penbutolol}

    P. Phukan and A. Sudalai, J. Chem. Soc., Perkin Trans. 1, 1999, 3015
    DOI: 10.1039/A902479D

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