79802-20-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-HydroxyMethylpyrrolidine HCl is used as a building block for the synthesis of pharmaceuticals and biologically active molecules. Its unique structure and reactivity make it an essential component in creating a variety of medicinal compounds.
Used as a Chiral Resolving Agent:
In the field of asymmetric synthesis, (S)-2-HydroxyMethylpyrrolidine HCl is utilized as a chiral resolving agent. This application is crucial for obtaining specific enantiomers of chiral molecules, which is significant in the development of enantiomerically pure drugs.
Used in Chemical Industry:
(S)-2-HydroxyMethylpyrrolidine HCl is employed as a ligand in asymmetric synthesis, playing a key role in the production of chiral auxiliaries. These auxiliaries are vital for the synthesis of enantiomerically pure compounds, which are essential in various chemical processes.
Used in Agrochemical Production:
(S)-2-HydroxyMethylpyrrolidine HCl also finds application in the agrochemical industry, where it is used in the production of chiral auxiliaries and agrochemicals. The ability of (S)-2-HydroxyMethylpyrrolidine HCl to participate in various chemical reactions makes it a valuable asset in developing effective and targeted agrochemicals.

Downstream Products

• 1571216-81-3 ethyl 4-(2-bromo-4-fluorophenyl)-6-(((S)-2-(hydroxymethyl)pyrrolidin-1-yl)methyl)-2-(1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylate 
• 438239-54-4 (S)-(1-cinnamylpyrrolidin-2-yl)methanol 
• 1448705-98-3 C₂₆H₂₇N₃OS 
• 108455-80-7 (S,Z)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)octadecan-9-en-1-one 

Relevant academic research and scientific papers

Chiral synthesis via organoboranes. 48. Efficient synthesis of trans- fused bicyclic and cyclic ketones and secondary alcohols in high optical purities via asymmetric cyclic hydroboration with isopinocampheylchloroborane etherate

Highly stereo- and enantioselective annelation has been achieved for the synthesis of trans-fused bicyclic and cyclic ketones via the asymmetric cyclic hydroboration of suitable cyclic dienes, such as 1-allyl-1- cycloalkenes or 1-vinyl-1-cycloalkenes and appropriate acyclic 1,4-dienes, respectively, with enantiomerically pure isopinocampheylchloroborane etherate (IpcBHCl·Et2O). The IpcBHCl· Et2O (an 86-90% equilibrium mixture) was readily synthesized by the reaction of an equivalent amount of hydrochloric acid in ethyl ether (Et2O) with optically pure isopinocampheylborane (IpcBH2). The hydroboration of the terminal double bond of a representative diene with IpcBHCl·Et2O readily provided the corresponding isopinocampheylalkylchloroborane (IpcRBCl). Subsequent hydridation of the IpcRBCl with lithium aluminum hydride (LAH, 0.25 equiv) at -20 or -25 °C generated the intermediate isopinocampheylalkylborane (IpcRBH) almost instantly, which then underwent a rapid stereospecific and enantioselective intramolecular cyclic hydroboration to provide the intermediate cyclic trialkylborane. This trialkylborane, on treatment with an aldehyde, liberated the optically pure auxiliary as α-pinene (readily recovered for recycle) to provide the corresponding cyclic borinate ester. This ester reacted smoothly with α,α-dichloromethyl methyl ether (DCME) in the presence of a hindered base (the DCME reaction) to yield, after oxidation with buffered hydrogen peroxide, the trans-fused bicyclic or cyclic ketone in high enantiomeric excess (ee). In another improved approach, in situ generated IpcBHCl·Et2O, from the reduction of isopinocampheyldichloroborane (IpcBCl2) with trimethylsilane (Me3SiH), in the presence of representative dienes in Et2O provided considerably improved optical yields of the bicyclic and cyclic ketones. The trialkylboranes obtained from suitable acyclic dienes can be easily protonolyzed to provide the secondary alcohols in high ee.