206264-81-5

Basic information

• Product Name: Cyclopenta[b]pyrrole-1(2H)-ethanethiol, hexahydro--ba--methyl-, (-ba-S,3aS,6aS)- (9CI)
• Synonyms: Cyclopenta[b]pyrrole-1(2H)-ethanethiol,hexahydro--bta--methyl-,(-bta-S,3aS,6aS)-(9CI);Cyclopenta[b]pyrrole-1(2H)-ethanethiol, hexahydro--ba--methyl-, (-ba-S,3aS,6aS)- (9CI);Cyclopenta[b]pyrrole-1(2H)-ethanethiol, hexahydro--b
• CAS NO: 206264-81-5
• Molecular Formula: C10H19NS
• Molecular Weight: 185.32956
• Product Categories: CYCLOPENTANE
• Mol File: 206264-81-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopenta[b]pyrrole-1(2H)-ethanethiol, hexahydro--ba--methyl-, (-ba-S,3aS,6aS)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopenta[b]pyrrole-1(2H)-ethanethiol, hexahydro--ba--methyl-, (-ba-S,3aS,6aS)- (9CI)(206264-81-5)
• EPA Substance Registry System: Cyclopenta[b]pyrrole-1(2H)-ethanethiol, hexahydro--ba--methyl-, (-ba-S,3aS,6aS)- (9CI)(206264-81-5)

Safety Data

• Hazardous Substances Data: 206264-81-5(Hazardous Substances Data)

Upstream product

• 20826-94-2 ethyl (2-oxocyclopentyl)acetate 
• 206264-79-1 (2S,1'S,5'S)-(-)-[2-(2'-Azabicyclo[3.3.0]octan-2'-yl)propyl]thioacetate 
• 206264-50-8 (4S,8R,11S)-(+)-4-Methyl-9-oxa-1-azatricyclo[6.3.0.0^4,8]undecan-2-one 
• 206264-66-6 (2S,1'S,5'S)-2-(2'-azabicyclo<3.3.0>oct-2'-yl)propanol 

Relevant articles and documents

Utilization of industrial waste materials. Part 14.? Synthesis of -amino alcohols and thiols with a 2-azabicyclo[3.3.0]octane backbone and their application in enantioselective catalysis

New, chiral β-tert-amino tert-alcohols have been synthesized from the enantiomerically pure sec-amine (all-R)-lb via the new glycine, alanine and phenylglycine derivatives 2-6. Grignard additions to these esters provided the new rigid amino alcohols 7-11 in fair yields. The absolute configurations of the stereogenic centers, which arose during the alkylation step, were assigned by an independent route leading to some of the optical antipodes of 7-10. Condensation of enantiomerically pure β-amino alcohols 13a-g, 16 and 17 with y-ketoester rac-12 afforded the TV; O-acetals 14a-g, 18 and 19, which were subsequently reduced to the β-/e/7-amino alcohols 10a,c and 15a-g. X-Ray analysis of compound 19 was performed to verify the stereochemistry observed by chemical correlation. The nucleophilic ring opening of enantiomerically pure styrene oxide by amine Ib resulted in the formation of regioisomeric amino alcohols 9a, 21a, and lOa, 21b. Amino thiol derivatives 22 and 25a,b were prepared by treatment of 10a-and 15a,b, respectively, with methanesulfonyl chloride followed by regio- and stereoselective cleavage of the situ formed aziridinium ions with potassium thioacetate. Reduction of these compounds to thiols 23 and 26a,b and subsequent oxidation afforded amino disulfides 24 and 27a,b. Finally, the bicyclic β-amino alcohols and thiols were used as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde and ee values up to 96% were found. ;.

Functionalized 2-azabicyclo[3.3.0]octanes as ligands in the enantioselective catalysis

Enantiopure compounds 4 were prepared by condensation of β- aminoalcohols 2 with ethyl (2-oxocyclopentyl)acetate 1 and subsequent reduction of intermediates 3. Compound 4a was converted to 6 via 5. With compounds 4, 5 or 6 as chiral ligands in the reaction of benzaldehyde with diethylzine an enantiomeric excess between 14 and 84% was achieved.