706806-60-2

Usage

Uses

Used in Pharmaceutical Industry:
BOC-(R)-ALPHA-BENZYL-PROLINE is used as a chiral building block for the synthesis of pharmaceuticals and biologically active molecules. Its unique three-dimensional shape and the presence of the BOC protecting group make it a valuable component in the development of new drugs with enhanced efficacy and selectivity.
Used in Organic Synthesis:
In the field of organic synthesis, BOC-(R)-ALPHA-BENZYL-PROLINE is employed as a key intermediate for the production of enantiomerically pure compounds. Its role in asymmetric synthesis allows chemists to introduce chirality into molecules, which is crucial for the creation of biologically active compounds with specific stereochemistry.
Used in Research and Development:
BOC-(R)-ALPHA-BENZYL-PROLINE is utilized in research and development for the exploration of new synthetic routes and methodologies. Its unique properties and reactivity make it a valuable tool for studying the synthesis of complex organic molecules and the development of novel catalysts and reagents.
Used in the Production of Enantiomerically Pure Compounds:
BOC-(R)-ALPHA-BENZYL-PROLINE is used as a chiral auxiliary in the production of enantiomerically pure compounds. Its ability to introduce chirality into molecules is essential for the synthesis of compounds with specific stereochemistry, which is often required for biological activity and selectivity in various applications, including pharmaceuticals and agrochemicals.

InChI:InChI=1/C17H23NO4/c1-16(2,3)22-15(21)18-11-7-10-17(18,14(19)20)12-13-8-5-4-6-9-13/h4-6,8-9H,7,10-12H2,1-3H3,(H,19,20)/t17-/m1/s1

Upstream product

• 118916-60-2 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 
• 620-05-3 iodomethylbenzene 
• 220200-89-5 (2R,5R)-5-benzyl-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 86116-84-9 (R)-2-benzylpyrrolidine-2-carboxylic acid 

Downstream Products

• 1033818-73-3 (R)-2-benzyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 1242094-36-5 C₂₃H₂₆BrN₃O₂ 

Relevant academic research and scientific papers

Palladium-Catalyzed Enantioselective C(sp3)-H Arylation of 2-Propyl Azaaryls Enabled by an Amino Acid Ligand

A palladium(II)-catalyzed enantioselective arylation of unbiased secondary C(sp3)-H bonds was developed. The enantioselectivity was controlled by the combination of a pyridyl or isoquinolinyl directing group and an amino acid, N-Boc-2-pentyl proline. A variety of 2-propyl azaaryls and biaryl iodides were employed to provide arylated products in moderate to good yields (up to 82%) with high enantioselectivities (up to 93:7 er). This reaction is a rare example of an amino-acid-enabled enantioselective acyclic methylene C(sp3)-H arylation. Furthermore, the reaction proceeded with high enantioselectivity even on a gram scale, and the product was transformed to a 5,6,7,8-tetrahydroisoquinoline bioactive molecule. Kinetic isotope effect (KIE) experiments indicated that C-H activation is the rate-determining step for the enantioselective C(sp3)-H arylation.

Aryl pyrrolidinyl and piperidinyl ketone derivatives and uses thereof

Aryl and heteroaryl ketone compounds substituted with pyrrolidines and piperidines, that modulate serotonin norepinephrine and/or dopamine neurotransmission. Also provided are pharmaceutical compositions, methods of using, and methods of preparing the com

Heteroaryl pyrrolidinyl and piperidinyl ketone derivatives and uses thereof

Compounds of the formula: or pharmaceutically acceptable salts thereof, wherein m, n, Ar, R1, R2, Ra and Rb are defined herein. Also provided are pharmaceutical compositions, methods of using, and methods of pre