Trimethylaluminium mediated amide bond formation in a continuous flow microreactor as key to the synthesis of rimonabant and efaproxiral.
A safe, functional-group-tolerant and high-throughput version of the trimethylaluminium mediated amide bond formation reaction has been developed in a microreactor system; rimonabant and efaproxiral were prepared to illustrate the utility of the method.
Gustafsson
Tomas
T
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich, Switzerland.
Pontén
Fritiof
F
Seeberger
Peter H
PH
D000473:Alkanes / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D004867:Equipment Design; D008872:Microwaves; D008904:Miniaturization; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D000077285:Rimonabant; D013237:Stereoisomerism
D000473:Alkanes; D000577:Amides; D000814:Aniline Compounds; D010880:Piperidines; D011422:Propionates; D011720:Pyrazoles; D000535:Aluminum; C067396:efaproxiral; D000077285:Rimonabant