637020-57-6

Basic information

• Product Name: (S)-ALPHA-BENZYL-PROLINE-HCL
• Synonyms: (S)-ALPHA-BENZYL-PROLINE-HCL;(S)-a-Benzylproline·HCl;(S)-a-Benzyl-prolineCl;(S)-2-Benzyl-DL-proline hydrochloride, 95%;2-Benzyl-D-proline hydrochloride, 95%;(S)-Alpha-Benzyl-ProHCl;(2S)-2-benzyl-2-pyrrolidinecarboxylic acid
• CAS NO: 637020-57-6
• Molecular Formula: C12H16ClNO2
• Molecular Weight: 241.71
• Mol File: 637020-57-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 389.8 °C at 760 mmHg
• Flash Point: 189.5 °C
• Appearance: /
• Density: 1.181±0.06 g/cm3(Predicted)
• Vapor Pressure: 8.95E-07mmHg at 25°C
• PKA: 2.31±0.20(Predicted)
• CAS DataBase Reference: (S)-ALPHA-BENZYL-PROLINE-HCL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-ALPHA-BENZYL-PROLINE-HCL(637020-57-6)
• EPA Substance Registry System: (S)-ALPHA-BENZYL-PROLINE-HCL(637020-57-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• Hazardous Substances Data: 637020-57-6(Hazardous Substances Data)

Usage

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-;/m0./s1

Upstream product

• 619306-99-9 (S)-N-(tert-butoxycarbonyl)-α-benzylproline ethyl ester 
• 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 

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.

OPTICALLY ACTIVE CYCLIC AMINO ACID DERIVATIVE, ITS INTERMEDIATE AND THEIR MANUFACTURING METHODS

PROBLEM TO BE SOLVED: To provide a new cyclic amino acid derivative useful as a synthetic intermediate for drugs and agricultural chemicals, its intermediate, and a method of manufacturing the compound having high general-purpose properties which can be applied to 4- to 6-membered rings and can obtain a target product with an extremely high optical selectivity. SOLUTION: The optically active amino acid derivative represented by formula (1) is obtained by derivatizing an optically active amino acid represented by formula (3) as a raw material to an N-haloalkylamino acid derivative represented by formula (2) and reacting the compound with a base.

An improved method of oxazolidinone hydrolysis in the asymmetric synthesis of α-alkylprolines

An improvement in Seebach's method for the synthesis of α-alkylprolines is reported wherein the hydrolysis of the chiral oxazolidinone 2 is performed on a suspension of silica gel in MeOH/H2O. Following hydrolysis, the pure α-alkylproline can be obtained by filtration thereby avoiding a tedious ion exchange purification.