Can I read An efficient synthesis of (R)-(+)- and (S)-(-)-propranolol from resolved 5-idomethyloxazo-lidin-2-ones on EtoBox?

An efficient synthesis of (R)-(+)- and (S)-(-)-propranolol from resolved 5-idomethyloxazo-lidin-2-ones by Giuliana Cardillo; Mario Orena; Sergio Sandri; Claudia Tomasini is a Chemistry article available to read on EtoBox.

What is An efficient synthesis of (R)-(+)- and (S)-(-)-propranolol from resolved 5-idomethyloxazo-lidin-2-ones about?

~1'So,5S.R)-3-(1'-phenyleth-l'-yl~-5-iodomethyloxazolidin-2-ones. s,b, have been synthesized and easily resolved by silica gel chromatography. Each pure diastereomer has been then converted to (Sl-(-)-propranolol + and (Rl-(+)-propranolol g. respectively. An empirical correlation of configuration and H NMR chemical shift for alternate diastereomers has been devised and has proved to be applicable in assigning the configuration of 5-substituted 3-(l'-phenyleth-l'-ylloxazolidin-2-ones. In a previous study 1 the growing importance of aminoalcohols in organic synthesis. due to the presence of this moiety in many biologically active compounds, prompted us to realize the synthesis of (5R,S)-5-(iodomethylloxasolidin-2-ones through the iodocyclofunctionalixation of allylic amines, in order to easily obtain 3-amino-1,2-diols and aminoalcohols. In this paper we report an efficient resolution 2 of the diastereomeric mixture of (lS\*,5S,R)-3-~l'-phenyleth-l'-yl)-5-(iodomethyl~oxazolidin-2-ones s,b, utilizing the commercially available (S)-1-phenylethylamine as the optically active portion of the molecule. 3 These intermediates are successively converted into the pure (S)-(-l-propranolol & and

Who reads An efficient synthesis of (R)-(+)- and (S)-(-)-propranolol from resolved 5-idomethyloxazo-lidin-2-ones?

Author

Giuliana Cardillo; Mario Orena; Sergio Sandri; Claudia Tomasini

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1987

Language

EN

Field

Chemistry (Physical Sciences)