138371-91-2

Upstream product

• 33485-71-1 2-oxopiperidine-1-carboxylic acid ethyl ester 
• 64-17-5 ethanol 
• 675-20-7 piperidin-2-one 

Downstream Products

• 497-88-1 sedamine 
• 70561-76-1 (±)-allosedamine 
• 138371-93-4 (1SR,2SR) N-ethoxycarbonyl-2-(β-hydroxy-β-phenylethyl)piperidine 
• 138371-93-4 (1RS,2SR) N-ethoxycarbonyl-2-(β-hydroxy-β-phenylethyl)piperidine 
• 24159-07-7 dl-febrifugine 
• 177980-28-8 7-Oxa-2-aza-bicyclo[4.1.0]heptane-2-carboxylic acid ethyl ester 
• 138371-92-3 N-ethoxycarbonyl-2-phenacylpiperidine 

Relevant academic research and scientific papers

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed amidoalkylation of silylenolethers. Stereocontrolled syntheses of (+/-)-sedamine and (+/-)-norsedamine

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl- and N-tert-butoxycarbonyl-2-ethoxypiperidines (3a and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (±)-sedamine (8) is described.

The preparation of α-substituted, β-hydroxy piperidines and pyrrolidines: The total synthesis of febrifugine

Epoxides generated from cyclic ene carbamates are effective N-acyl iminium ion precursors and allow for the preparation of β-hydroxy, α-substituted piperidines and pyrrolidines. The total synthesis of racemic Febrifugine is also described.