122875-06-3

Upstream product

• 77515-68-5 1-azaspiro<5.5>undecan-8-one 
• 1885-14-9 phenyl chloroformate 
• 77515-67-4 1-methoxy-5-(4'-aminobutyl)cyclohexa-1,3-diene 

Downstream Products

• 122875-11-0 (1R,9S)-8-Oxa-6-aza-tricyclo[7.3.1.0^1,6]tridecan-7-one 
• 122875-08-5 (6R,8R)-8-Hydroxy-1-aza-spiro[5.5]undecane-1-carboxylic acid phenyl ester 
• 122875-08-5 (6R,8S)-8-Hydroxy-1-aza-spiro[5.5]undecane-1-carboxylic acid phenyl ester 

Relevant academic research and scientific papers

Studies on the Synthesis of 1-Azaspiroundecanes Related to Histrionicotoxin

3-Methoxybenzaldehyde was converted into 4-(3-methoxyphenyl)butylamine (4), and the derived hydrochloride was reduced with Li/NH3/EtOH to give the spirocyclic keto amine 6.The reduction of 6 and urethane derivatives 13 and 14 to give the corresponding cis and trans alcohols 9/10, 15/16, and 17/18 was studied.The keto amine 6 upon attempted ketalization underwent rearrangement to give the α,β-unsaturated imine 11.Treatment of 6 with N-chlorosuccinimide, followed by DBU, gave the aziridine 21.The amide 25 was converted derectly into 1-azaspiroundecane-2,8-dione (24) by Birch reduction and acid hydrolysis.The dione 24 underwent stereospecific reduction with LS-Selectride to give the cis alcohol 30.