66643-45-6

Basic information

• Product Name: ethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
• Synonyms: ethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
• CAS NO: 66643-45-6
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.2
• Mol File: 66643-45-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate(66643-45-6)
• EPA Substance Registry System: ethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate(66643-45-6)

Safety Data

• Hazardous Substances Data: 66643-45-6(Hazardous Substances Data)

Upstream product

• 52003-32-4 ethyl 1,2,3,6-tetrahydropyridine-1-carboxylate 
• 66643-46-7 ethyl 4-bromo-3-hydroxypiperidine-1-carboxylate 
• 40240-12-8 1-benzyl-1,2,3,6-tetrahydropyridine 
• 2876-13-3 N-benzylpyridinium chloride 
• 110-86-1 pyridine 
• 694-05-3 1,2,3,6-tetrahydropyridine 
• 66643-44-5 ethyl 4-(2-(4-methylphenylsulfonyl)hydrazono)piperidine-1-carboxylate 
• 29976-53-2 N-ethoxycarbonyl-4-piperidone 

Downstream Products

• 114870-50-7 ethyl trans-3-azido-4-hydroxy-1-piperidinecarboxylate 
• 907545-69-1 ethyl trans-4-azido-3-hydroxy-1-piperidinecarboxylate 
• 66643-47-8 ethyl 3-acetoxy-4-bromopiperidine-1-carboxylate 
• 66643-49-0 ethyl 3-hydroxy-1,2,3,6-tetrahydropiperidine-1-carboxylate 
• 66643-46-7 ethyl trans-4-bromo-3-hydroxy-1-piperidinecarboxylate 
• 66643-46-7 ethyl 4-bromo-3-hydroxypiperidine-1-carboxylate 

Relevant articles and documents

Total synthesis of (±)-20: S -hydroxy-1,2-dehydro-pseudoaspidospermidine via a C-H activation/transannular cyclization strategy

A total synthesis to the pseudoaspidospermidine family via a C-H activation/transannular cyclization strategy has been accomplished. The applicability of this approach is showcased in the concise synthesis (ten steps) of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine (4) starting from literature known compound 11. Via a joint synthetic sequence we were also able to address the related iboga alkaloid (±)-isovelbanamine (7) in nine steps. Key features of this synthesis are a transannular cyclization to generate the pseudoaspidospermidine skeleton (C-H activation) and a Witkop photocyclization reaction providing a 9-membered lactam. It is also worth mentioning that the joint synthetic sequence can be carried out on a multigram scale.

Development of two diastereoselective routes towards trans-4-aminomethyl-piperidin-3-ol building blocks

Two diastereoselective, scaleable routes towards trans-3,4-disubstituted piperidines with a 4-hydroxymethyl-3-hydroxy or 4-aminomethyl-3-hydroxy substitution pattern are being described. In the first route, the 3,4-trans configuration was introduced regio- and diastereoselectively via a hydroboration/oxidation sequence starting from 4-hydroxymethylpyridine. In the second route, regioselective epoxide ring opening of N-benzyl-3,4-epoxy-piperidine was achieved with LiCN, in situ generated from acetocyanohydrin and LiNH2. The regioselectivity of both the hydroboration and the epoxide ring opening was positively influenced by the presence of the basic piperidine nitrogen. Both routes have been optimized to be performed at large scale.

Practical synthesis of ethyl cis-4-amino-3-methoxy-1-piperidine carboxylate, a key intermediate of cisapride

A practical synthesis of ethyl cis-4-amino-3-methoxy-1piperidinecarboxylate 1, a key intermediate of cisapride as a potent gastrointestinal stimulant, has been accomplished from 1-methyl-1,2,3,6-tetrahydropyridine 2 via an efficient formation of cis-fused oxazolidinopiperidine 7.