135500-40-2

Upstream product

• 135384-13-3 (R)-1-Benzyl-1-aza-spiro[5.5]undec-8-en-7-one 
• 88056-92-2 (-)-2-cyano-6-phenyloxazolopiperidine 
• 135384-11-1 1-[(R)-1-Benzyl-2-(2-[1,3]dioxolan-2-yl-ethyl)-piperidin-2-yl]-ethanol 
• 135384-12-2 1-[(R)-1-Benzyl-2-(2-[1,3]dioxolan-2-yl-ethyl)-piperidin-2-yl]-ethanone 
• 135384-10-0 1-[(R)-2-(2-[1,3]Dioxolan-2-yl-ethyl)-1-((R)-2-hydroxy-1-phenyl-ethyl)-piperidin-2-yl]-ethanol 
• 127708-18-3 (3R,5R,8aR)-5-(2-[1,3]Dioxolan-2-yl-ethyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile 
• 100-39-0 benzyl bromide 

Downstream Products

• 135384-14-4 (6R,7R)-1-Benzyl-7-butyl-1-aza-spiro[5.5]undecan-7-ol 
• 135500-41-3 (S)-1-Benzyl-7-butyl-1-aza-spiro[5.5]undec-7-ene 
• 135500-42-4 (6R,7S,8S)-1-Benzyl-7-butyl-1-aza-spiro[5.5]undecan-8-ol 
• 135500-43-5 (6R,7R,8R)-1-Benzyl-7-butyl-1-aza-spiro[5.5]undecan-8-ol 

Relevant academic research and scientific papers

Formal Synthesis of (–)-Perhydrohistrionicotoxin Using a Thorpe-Ziegler Cyclization Approach. Synthesis of Functionalized Aza-Spirocycles

The formal synthesis of (–)-PHTX is described. Our approach was based on the anodic cyanation of (S)-1-(1-phenylethyl)-piperidine (–)-1 to afford α-aminonitrile 2 in 85 % yield in a 53:47 dr. The presence of the α-phenylethyl group as the chiral auxiliary

Rearrangement of α-hydroxy imines to α-amino ketones: Mechanistic aspects and synthetic applications

In refluxing diglyme, rearrangement of α-hydroxy imines bearing diversely substituted allyl groups or a 3-trimethylsilylpropargyl group on the α-carbon to the nitrogen afforded in good yields α-amino ketones. Migration of allyl or 3-trimethylsilylallyl groups occurred without allylic transposition in contrast to be 1-methylallyl group. In the 3 cases studied, the rearrangement of enantioenriched α-hydroxy imines took place with complete 1,2-chirality transfer. The rearrangement was applied to the preparation of (+)-1-benzyl-1-azaspiro[5.5]undecan-7-one, a precursor in the synthesis of (-)-perhydrohistrionicotoxin.

Thermal Rearrangement of Enantioenriched α-Hydroxy Imines -II. Formal Synthesis of (-)-Perhydrohistrionicotoxin.

Synthesis of (+)-1-benzyl-1-azaspiroundecan-7-one 6 from α-ketol 1, via a 1,2-suprafacial chirality transfer, is described.

Asymmetricsynthesis. XXXII. Formalsynthesisof (-) - Perhydrohistrionicotoxin

The synthesis of (-)-depentylperhydrohistrionicotoxin 2 from the 2-cyano-6-oxazolopiperidine synthon (-) 3 has been achieved. The spiro skeleton was formed by an aldol cyclization of a methyl ketone and an aldehyde function belonging to chains borne at C-