Novel optically active chroman derivatives, their preparation and novel intermediates

US4645845A · kind A · utility

Assignee

• BASF SE

Inventors

• Henning-Peter Gehrken · Lambsheim, DE
• Hansgeorg Ernst · Speyer, DE
• Joachim Paust · Schifferstadt, DE

Key dates

• Filing date: Mar 12, 1984
• Grant date: Feb 24, 1987
• Expiry date: Mar 12, 2004

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/72
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Novel optically active chroman derivatives of the general formulae Ia and Ib ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen or alkyl and X is --OH, --O--CO-alkyl, --O-alkyl, --O-tosyl, --O-mesyl, --O-benzenesulfonyl, Cl, Br or I, are prepared by a process in which PA0 (a) the racemate of the formula I' ##STR2## is esterified in the side chain with a carboxylic acid and then acylated with an optically active carboxylic acid halide of the general formula III ##STR3## or with the corresponding carboxylic anhydride, to give a chroman derivative IV ##STR4## or (b) the racemate I' is esterified in the side chain with the carboxylic acid from which III is derived, and, if required, the resulting ester is acylated with a carboxylic acid halide to give IV' ##STR5## the resulting mixture IV or IV', which consists of two diastereomers, is resolved by fractional crystallization, the diastereomers are hydrolyzed to the alcohols Ia and Ib and, if desired, these are converted to the other compounds Ia and Ib in a conventional manner. Useful optically active chroman derivatives Ia and Ib and diastereomeric chromanyl esters IV and IV' are also claimed.