347189-06-4

Basic information

• Product Name: (2R,5R)-1-(tert-butoxycarbonyl)-5-[(S)-methoxycarbonyl(4-bromophenyl)methyl]proline methyl ester
• Synonyms: (2R,5R)-1-(tert-butoxycarbonyl)-5-[(S)-methoxycarbonyl(4-bromophenyl)methyl]proline methyl ester
• CAS NO: 347189-06-4
• Molecular Weight: 456.334
• Mol File: 347189-06-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,5R)-1-(tert-butoxycarbonyl)-5-[(S)-methoxycarbonyl(4-bromophenyl)methyl]proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-1-(tert-butoxycarbonyl)-5-[(S)-methoxycarbonyl(4-bromophenyl)methyl]proline methyl ester(347189-06-4)
• EPA Substance Registry System: (2R,5R)-1-(tert-butoxycarbonyl)-5-[(S)-methoxycarbonyl(4-bromophenyl)methyl]proline methyl ester(347189-06-4)

Safety Data

• Hazardous Substances Data: 347189-06-4(Hazardous Substances Data)

Upstream product

• 73323-65-6 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate 
• 264881-99-4 methyl 2-(4-bromophenyl)-2-diazoacetate 
• 145681-01-2 (+/-)-N-tert-butoxycarbonylproline methyl ester 

Downstream Products

• 347188-97-0 (2R,5R)-5-[(S)-methoxycarbonyl(4-bromophenyl)methyl]proline methylester 

Relevant articles and documents

New strategic reactions for organic synthesis: Catalytic asymmetric C-H activation α to nitrogen as a surrogate for the Mannich reaction

The asymmetric C-H activation reactions of methyl aryldiazoacetates are readily induced by the rhodium prolinate catalyst Rh2(S-DOSP)4 (1) or the bridged prolinate catalysts Rh2(S-biDOSP)2 (2a) and Rh2(S-biTISP)2 (2b). The C-H activation of N-Boc-protected cyclic amines demonstrates that the donor/acceptor-substituted carbenoids display remarkable chemoselectivity, which allows for highly regioselective, diastereoselective, and enantioselective reactions to be achieved. Furthermore, the reactions can display high levels of double stereodifferentiation and kinetic resolution. The C-H activation is caused by a rhodium carbenoid induced C-H insertion. The potential of this chemistry is demonstrated by a very direct synthesis of threo-methylphenidate.