111492-61-6

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-benzoyl-, 1,1-dimethylethyl ester, (2S)-
• CAS NO: 111492-61-6
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.348
• Mol File: 111492-61-6.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-benzoyl-, 1,1-dimethylethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-benzoyl-, 1,1-dimethylethyl ester, (2S)-(111492-61-6)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-benzoyl-, 1,1-dimethylethyl ester, (2S)-(111492-61-6)

Safety Data

• Hazardous Substances Data: 111492-61-6(Hazardous Substances Data)

Upstream product

• 111492-59-2 C₂₂H₂₆NO₅P 
• 24424-99-5 di-tert-butyl dicarbonate 
• 69610-41-9 Boc-L-Pro-H 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 38111-44-3 phenylzinc(II) bromide 
• 100-58-3 phenylmagnesium bromide 
• 147-85-3 L-proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 1499-21-4 Diphenylphosphinic chloride 

Downstream Products

• 106202-17-9 ethyl (S)-2-benzoylpyrrolidine-1-carboxylate 

Relevant articles and documents

Diastereoselective Synthesis of Nonplanar 3-Amino-1,2,4-oxadiazine Scaffold: Structure Revision of Alchornedine

Herein, we report the diastereoselective synthesis of a 3-amino-1,2,4-oxadiazine (AOXD) scaffold. The presence of a N-O bond in the ring prevents the planar geometry of the aromatic system and induces a strong decrease in the basicity of the guanidine moiety. While DIBAL-H appeared to be the most efficient reducing agent because it exhibited high diastereoselectivity, we observed various behaviors of the Mitsunobu reaction on the resulting β-aminoalcohol, leading to either inversion or retention of the configuration depending on the steric hindrance in the vicinity of the hydroxy group. The physicochemical properties (pKa and log D) and hepatic stability of several AOXD derivatives were experimentally determined and found that the AOXD scaffold possesses promising properties for drug development. Moreover, we synthesized alchornedine, the only natural product with the AOXD scaffold. Based on a comparison of the analytical data, we found that the reported structure of alchornedine was incorrect and hypothesized a new one.

Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine, and Weinreb “Amine”

The well-established Hoppe–Beak chemistry, which involves enantioselective generation of organolithium compounds in the presence of (?)-sparteine, was revisited and applied to unprecedented acylations with Weinreb amides to access highly enantioenriched α-oxyketones and cyclic α-aminoketones. Recycling of the sustainable solvent cyclopentyl methyl ether, sparteine, and the released Weinreb “amine” [HNMe(OMe)] was possible through a simple work-up procedure that enabled full recovery of these precious materials. The methodology features a robust scope and flexibility, thus allowing the enantioselective preparation of scaffolds amenable of further derivatization.

Synthesis method of natural product (-)-newbouldine

The invention discloses a synthesis method of a natural product (-)-newbolline. With optically-active Boc protected pyrrolidine formamide as a raw material, five chemical conversion processes are successively carried out, namely, a Grignard reaction, a Wi