Practical Diastereoselective Synthesis and Scale-up Study of (+)-2-((1R,2R,3R,5S)-2-Amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)ethanol: A Key Intermediate of the Novel Prostaglandin D2 Receptor Antagonist S-5751

Autor:	Tetsuo Okada, Aiko Hasegawa, Katsuo Oda, Tsunetoshi Honma, Hideo Nogusa, Hiroshi Hashizume, Makoto Kakinuma, Toshiaki Masui, Yoshiharu Hiramatsu, Takemasa Hida, Kyozo Kawata, Susumu Mitsumori
Rok vydání:	2009
Předmět:	Ethyl bromoacetate chemistry.chemical_compound Heptane Ethanol Chemistry Stereochemistry Organic Chemistry Antagonist Physical and Theoretical Chemistry Alkylation Ring (chemistry) Oxime Prostaglandin D2 receptor
Zdroj:	Organic Process Research & Development. 13:1413-1418
ISSN:	1520-586X 1083-6160
Popis:	A new synthetic process was developed for (+)-2-((1R,2R,3R,5S)-2-amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)ethanol, a key intermediate of S-5751. Diastereoselective alkylation of (+)-nopinone with ethyl bromoacetate, formation of O-methyl oxime, and diastereoselective reduction with NaBH4−AlCl3 could be safely carried out. Stereochemistry of the (1R,2R,3R,5S)-6,6-dimethylbicyclo[3.1.1]heptane ring was discussed to achieve high diastereoselectivity on these reactions. For the scale-up, detailed consideration was given to the safety of the NaBH4−AlCl3 reduction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::633f938196c49287624b268a956487ea https://doi.org/10.1021/op9001092 Zobrazit plný text záznamu