Practical chemical and enzymatic technologies for (S)-1, 4-benzodioxan-2-carboxypiperizine intermediate in the synthesis of (S)-doxazosin mesylate

…, FX McConville, RF Rossi, DJ Olsson, DW Kessler…

Index: Fang; Grover, Paul; Han, Zhengxu; McConville, Fran X.; Rossi, Richard F.; Olsson, Damase J.; Kessler, Donald W.; Wald, Stephen A.; Senanayake, Chris H. Tetrahedron Asymmetry, 2001 , vol. 12, # 15 p. 2169 - 2174

Full Text: HTML

Citation Number: 26

Abstract

(S)-1, 4-Benzodioxan-2-carboxypiperazine (S)-2, the key chiral intermediate for the synthesis of (S)-doxazosin, was prepared utilizing two approaches:(i) enzymatic resolution of ethyl 1, 4-benzodioxan-2-carboxylate with an esterase (Serratia) followed by amide formation;(ii) direct resolution of 1, 4-benzodioxan-2-carboxypiperazine 2 with d-tartaric acid. An efficient process for the conversion of (S)-2 to (S)-doxazosin mesylate was developed ( ...

Related Articles:

A facile approach to chiral 1, 4-benzodioxane toward the syntheses of doxazosin, prosympal, piperoxan, and dibozane

[Rouf, Abdul; Aga, Mushtaq A.; Kumar, Brijesh; Taneja, Subhash Chandra Tetrahedron Letters, 2013 , vol. 54, # 48 p. 6420 - 6422]

Chemoenzymatic synthesis of piperoxan, prosympal, dibozane, and doxazosin

[Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. Tetrahedron Asymmetry, 2012 , vol. 23, # 22-23 p. 1615 - 1623]

A facile approach to chiral 1, 4-benzodioxane toward the syntheses of doxazosin, prosympal, piperoxan, and dibozane

[Rouf, Abdul; Aga, Mushtaq A.; Kumar, Brijesh; Taneja, Subhash Chandra Tetrahedron Letters, 2013 , vol. 54, # 48 p. 6420 - 6422]

A facile approach to chiral 1, 4-benzodioxane toward the syntheses of doxazosin, prosympal, piperoxan, and dibozane

[Rouf, Abdul; Aga, Mushtaq A.; Kumar, Brijesh; Taneja, Subhash Chandra Tetrahedron Letters, 2013 , vol. 54, # 48 p. 6420 - 6422]

More Articles...