146500-37-0

Basic information

• Product Name: L-Proline, 1-phenyl-, methyl ester
• CAS NO: 146500-37-0
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.257
• Mol File: 146500-37-0.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-phenyl-, methyl ester(146500-37-0)
• EPA Substance Registry System: L-Proline, 1-phenyl-, methyl ester(146500-37-0)

Safety Data

• Hazardous Substances Data: 146500-37-0(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 139983-29-2 (S)-1-phenylpyrrolidine-2-carboxylic acid 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 66003-76-7 Diphenyliodonium triflate 
• 591-50-4 iodobenzene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 147-85-3 L-proline 
• 108-86-1 bromobenzene 
• 67-56-1 methanol 
• 24738-81-6 (S)-methyl 1-cyclohexenylprolinate 
• 117846-71-6 methyl 5-(N-methyl-N-phenylamino)pentanoate 
• 758640-21-0 N-Benzylaniline 

Downstream Products

• 896462-45-6 (S)-1-(2-bromophenyl)-2-(methoxymethyl)pyrrolidine 
• 896462-37-6 (S)-(1-(2-bromophenyl)pyrrolidin-2-yl)methanol 
• 896462-48-9 (S)-2-(benzyloxymethyl)-1-(2-bromophenyl)pyrrolidine 
• 139983-29-2 (S)-1-phenylpyrrolidine-2-carboxylic acid 
• 1315457-05-6 C₁₁H₁₄BrN 
• 1315457-06-7 Br^(1-)*C₁₅H₂₀N₃⁽¹⁺⁾ 
• 4789-09-7 1-phenylpiperidin-2-one 
• 18133-14-7 2-(hydroxymethyl)-N-phenylpyrrolidine 
• 896462-34-3 ((S)-1-phenylpyrrolidin-2-yl)methanol 

Relevant articles and documents

Stereoretentive N-Arylation of Amino Acid Esters with Cyclohexanones Utilizing a Continuous-Flow System

The N-arylation of chiral amino acid esters with minimal racemization is a challenging transformation because of the sensitivity of the α-stereocenter. A versatile synthetic method was developed to prepare N-arylated amino acid esters using cyclohexanones as aryl sources under continuous-flow conditions. The designed flow system, which consists of a coil reactor and a packed-bed reactor containing a Pd(OH)2/C catalyst, efficiently afforded the desired N-arylated amino acids without significant racemization, accompanied by only small amounts of easily removable co-products (i. e., H2O and alkanes). The efficiency and robustness of this method allowed for the continuous synthesis of the desired product in very high yield and enantiopurity with high space-time yield (74.1 g L?1 h?1) and turnover frequency (5.9 h?1) for at least 3 days.

Iron-promoted dealkylative carbene aminocyclization of δ-arylamino-α-diazoesters

Herein, we report a novel methodology to accessN-aryl proline derivatives using amino-tethered α-diazoesters and cheap, readily available iron salts. Mechanistically, the aminocyclization reaction involves the initial formation of an iron-carbene complex followed by a nucleophilic attack of the aniline nitrogen atom to give an ammonium ylide intermediate, which finally undergoes the iron-promoted dealkylation.

Transition-Metal-Free Selective C?H Benzylation of Tertiary Arylamines by a Dearomatization-Aromatization Sequence

Due to the significance of hybrid systems in drug discovery, there is an urgent need to assemble multiple biologically active ingredients into a single molecule. Here, we report a general transition-metal-free selective C?H benzylation of tertiary arylamines in good to excellent yields with a broad substrate scope and high functional-group tolerance under mild conditions. Besides arylamines, some other benzene derivatives also readily furnished the corresponding diaryl methane derivatives with this protocol. A series of control experiments and theoretical calculations indicated that this transition-metal-free reaction is a dearomatization-aromatization process.