342793-00-4

Usage

Uses

Used in Pharmaceutical Research:
L-Proline, 1-(1-methylethyl)(9CI) is used as a chiral building block for the synthesis of various pharmaceuticals and natural products. Its unique structure and properties contribute to the development of new and innovative medications.
Used in Organic Synthesis:
In the field of organic synthesis, L-Proline, 1-(1-methylethyl)(9CI) serves as a key component in the creation of complex organic molecules, facilitating the synthesis of a wide range of compounds.
Used as a Chemical Intermediate:
L-Proline, 1-(1-methylethyl)(9CI) is utilized as a chemical intermediate in the production of various drugs and fine chemicals, playing a crucial role in the manufacturing process of these substances.

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 academic research and scientific papers

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.

Asymmetrie three-component strecker reactions catalyzed by trans-4-hydroxy-L-proline-derived N,N′-dioxides

Novel trans-4-hydroxy-L-proline-derived N,N′-dioxides have been developed and used as efficient organocatalysts for the one-pot three-component Strecker reaction with an aldehyde, (1,1-diphenyl)methylamine, and TMSCN. Both aromatic and aliphatic aldehydes

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.

Proline-based N-oxides as readily available and modular chiral catalysts. Enantioselective reactions of allyltrichlorosilane with aldehydes

(Chemical Equation Presented) A proline-based N-oxide is identified that serves as an effective catalyst for the reaction of allyltrichlorosilane with aryl and α,β-unsaturated aldehydes at room temperature to afford the desired homoallylic alcohols in up to 92% ee. The chiral catalyst can be easily prepared from optically pure proline in three simple steps and 60% overall yield.