86116-84-9

Basic information

• Product Name: (R)-ALPHA-BENZYL-L-PROLINE-HCL
• Synonyms: (R)-ALPHA-BENZYL-L-PROLINE-HCL;(R)-ALPHA-BENZYLPROLINE HCL;(R)-a-Benzyl proline·HCl;(R)-a-Benzyl-prolineCl;L-Proline, 2-(phenylMethyl)-;(R)-2-Benzyl-DL-proline hydrochloride, 95%;2-Benzyl-L-proline hydrochloride, 95%;(R)-2-benzyl-pyrrolidine-2-carboxylic acid
• CAS NO: 86116-84-9
• Molecular Formula: C12H16ClNO2
• Molecular Weight: 241.71
• Mol File: 86116-84-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 270-272℃
• Boiling Point: 361.2oC at 760 mmHg
• Flash Point: 172.3oC
• Appearance: /
• Density: 1.181±0.06 g/cm3(Predicted)
• Vapor Pressure: 7.53E-06mmHg at 25°C
• PKA: 2.31±0.20(Predicted)
• CAS DataBase Reference: (R)-ALPHA-BENZYL-L-PROLINE-HCL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-ALPHA-BENZYL-L-PROLINE-HCL(86116-84-9)
• EPA Substance Registry System: (R)-ALPHA-BENZYL-L-PROLINE-HCL(86116-84-9)

Safety Data

• Hazardous Substances Data: 86116-84-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C12H15NO2.ClH/c14-11(15)12(7-4-8-13-12)9-10-5-2-1-3-6-10;/h1-3,5-6,13H,4,7-9H2,(H,14,15);1H/t12-;/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 
• 86046-32-4 (R)-2-benzyl-N,N-dimethylpyrrolidine-2-carboxamide 
• 100-39-0 benzyl bromide 
• 24919-40-2 (S)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione 
• 870677-83-1 10-isopropyl-1,2,3,11a-tetrahydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione 
• 870677-85-3 11a-allyl-10-isopropyl-1,2,3,11a-tetrahydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione 
• 86046-13-1 (2R,5R)-5-benzyl-2-tert-butyl-1-aza-3-oxabicyclo<3.3.0>octan-4-one 

Downstream Products

• 1419208-67-5 (R)-(2-benzylpyrrolidin-2-yl)methanol 
• 706806-60-2 (R)-2-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 

Relevant articles and documents

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.

Highly enantioselective synthesis of rigid, quaternary 1,4-benzodiazepine- 2,5-diones derived from proline

(Chemical Equation Presented) Proline-derived 1,4-benzodiazepine-2,5-diones are extremely useful scaffolds in medicinal chemistry. In this paper, we describe a protocol for retentive C3 alkylation of these materials, thus accomplishing the direct synthesis of enantiopure quaternary 1,4-benzodiazepine-2,5-diones. The high enantioselectivities (up to 99.5%) are attributed to memory of chirality.