Process for the production of cyclopropane derivatives

US8497384B2 · kind B2 · utility

Assignee

• DSM Fine Chemicals Austria NFG GmbH & Co KG · AT

Inventors

• Mehul Thathagar · Geleen, NL
• Peter Poechlauer · Linz, AT
• Sascha Braune · Luftenberg an der Donau, AT

Key dates

• Filing date: Nov 12, 2009
• Grant date: Jul 30, 2013
• Expiry date: May 13, 2030

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/582
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of a cyclopropane derivative of Formula (I), by reacting an olefin of Formula (II), with a carbene of the formula:CR1R2, in a reaction vessel, optionally in the presence of a solvent, wherein, R1 and R2 are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, heterocyclyl, carbocyclyl, heterocyclyl, —C(O)R7 or —NR82; R3, R4, R5 and R6 are each independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, aryl, aryloxy, heteroaryl, heterocyclyl, carbocyclyl, heterocyclyl, —C(O)R9, —NR102, —SR11, —S(O)R11, or —SO2R11, or R3 and R6 are as defined above and R4 and R5 together form a ring, which ring is carbocyclyl, heterocyclyl, aromatic or heteroaromatic; R7 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, aryloxy, heteroaryl or —NR102; R8 is hydrogen, C1-C6 alkyl, C1-C6 alkenyl, aryl, heteroaryl, carbocyclyl or heterocyclyl; R9 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, aryloxy or heteroaryl; R10 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, carbocyclyl, heterocyclyl or C(O)R12; R11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, carbocyclyl or heterocyclyl; and R12 is hydrogen, hydroxy,…