The methyl ester of 1,4-benzodioxane-2-carboxylic acid 1 and the mesylate of 2-hydroxymethyl-1,4-benzodioxane 2 are synthetic intermediates whose enantiomers can be advantageously used to prepare a number of enantiopure 2-substituted 1,4-benzodioxanes from readily accessible (±)-1,4-benzodioxane-2-carboxilic acid. We have previously demonstrated the conglomerate nature of the enantiomeric systems of 1 and 2. Herein, we report the resolution of their racemates by preferential crystallization according to an entrainment procedure. In particular, the entrainment resolution of 1 showed good efficiency, which makes the present method a competitive alternative to the classical resolutions of 1,4-benzodioxane-2-carboxylic acid with dehydroabietylamine and para-substituted 1-phenylethylamines that we have recently reported

Resolution of 2-substituted 1,4-benzodioxanes by entrainment / C. Bolchi, M. Pallavicini, L. Fumagalli, C. Rusconi, M. Binda, E. Valoti. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 18:9(2007), pp. 1038-1041. [10.1016/j.tetasy.2007.04.026]

Resolution of 2-substituted 1,4-benzodioxanes by entrainment

C. Bolchi;M. Pallavicini;L. Fumagalli;C. Rusconi;E. Valoti
2007

Abstract

The methyl ester of 1,4-benzodioxane-2-carboxylic acid 1 and the mesylate of 2-hydroxymethyl-1,4-benzodioxane 2 are synthetic intermediates whose enantiomers can be advantageously used to prepare a number of enantiopure 2-substituted 1,4-benzodioxanes from readily accessible (±)-1,4-benzodioxane-2-carboxilic acid. We have previously demonstrated the conglomerate nature of the enantiomeric systems of 1 and 2. Herein, we report the resolution of their racemates by preferential crystallization according to an entrainment procedure. In particular, the entrainment resolution of 1 showed good efficiency, which makes the present method a competitive alternative to the classical resolutions of 1,4-benzodioxane-2-carboxylic acid with dehydroabietylamine and para-substituted 1-phenylethylamines that we have recently reported
Settore CHIM/08 - Chimica Farmaceutica
2007
http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THT-4NW1H78-7&_user=1080510&_coverDate=05%2F29%2F2007&_alid=595888000&_rdoc=1&_fmt=full&_orig=search&_cdi=5291&_sort=d&_docanchor=&view=c&_ct=1&_acct=C000051355&_version=1&_urlVersion=0&_userid=1080510&md5=8569ae5538eca13f0454a4ac5f10cd10
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/32353
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 23
  • ???jsp.display-item.citation.isi??? 22
social impact