342793-00-4

Basic information

• Product Name: L-Proline, 1-(1-methylethyl)- (9CI)
• Synonyms: L-Proline, 1-(1-methylethyl)- (9CI);1-isopropylproline;proline, 1-(1-methylethyl)-;(S)-1-isopropylpyrrolidine-2-carboxylic acid;1-isopropyl-L-proline(SALTDATA: FREE);1-Isopropyl-pyrrolidine-2-carboxylic acid;(2S)-1-(propan-2-yl)pyrrolidine-2-carboxylic acid;N-Isopropyl-L-proline
• CAS NO: 342793-00-4
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.2102
• EINECS: 1312995-182-4
• Product Categories: PYRROLE;CARBOXYLICACID;ISOPROPYL
• Mol File: 342793-00-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Proline, 1-(1-methylethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-(1-methylethyl)- (9CI)(342793-00-4)
• EPA Substance Registry System: L-Proline, 1-(1-methylethyl)- (9CI)(342793-00-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 342793-00-4(Hazardous Substances Data)

Usage

General Description

L-Proline, 1-(1-methylethyl)- (9CI) is a chemical compound that is also known as 1-isopropyl-L-proline. It is a derivative of the amino acid L-proline and is commonly used in organic synthesis and pharmaceutical research. Its molecular formula is C8H16NO2 and it is a white crystalline powder with a molecular weight of 156.21 g/mol. L-Proline, 1-(1-methylethyl)- (9CI) is used as a chiral building block in the synthesis of various pharmaceuticals and natural products due to its unique structure and properties. It is also used as a chemical intermediate in the production of various drugs and fine chemicals.

Upstream product

• 67-64-1 acetone 
• 147-85-3 L-proline 

Downstream Products

• 1169857-11-7 methyl (4R)-15-cyclohexyl-4-[(1-isopropyl-L-prolyl)amino]-5,6,8,9-tetrahydro-4H-indolo[1',2':4,5][1,4]diazepino[6,7,1-ij]quinoline-12-carboxylate 

Relevant articles and documents

Zinc catalyzed and mediated asymmetric propargylation of trifluoromethyl ketones with a propargyl boronate

The development of zinc-mediated and -catalyzed asymmetric propargylations of trifluoromethyl ketones with a propargyl borolane and the N-isopropyl-l-proline ligand is presented. The methodology provided moderate to high stereoselectivity and was successfully applied on a multikilogram scale for the synthesis of the Glucocorticoid agonist BI 653048. A mechanism for the boron-zinc exchange with a propargyl borolane is proposed and supported by modeling at the density functional level of theory. A water acceleration effect on the zinc-catalyzed propargylation was discovered, which enabled a catalytic process to be achieved. Reaction progress analysis supports a predominately rate limiting exchange for the zinc-catalyzed propargylation. A catalytic amount of water is proposed to generate an intermediate that catalyzes the exchange, thereby facilitating the reaction with trifluoromethyl ketones.

Dual mechanism of zinc-proline catalyzed aldol reactions in water

The aldol reaction of acetone with aldehydes in aqueous medium under catalysis by zinc-proline (Zn(l-Pro)2) and secondary amines such as proline, (2S,4R)-4-hydroxyproline (Hyp) and (S)-(+)-1-(2-pyrrolidinomethyl) pyrrolidine (PMP) is shown to proceed by an enamine mechanism, as evidenced by reductive trapping of the iminium intermediate, while the aldol reaction of dihydroxyacetone (DHA) under catalysis by zinc-proline and by general bases such as N-methylmorpholine (NMM) is shown to occur under rate-limiting deprotonation of the α-carbon and formation of an enolate intermediate. The Royal Society of Chemistry 2006.