885462-68-0

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2S')-α-(pyrrolidin-2-yl)benzyl alcohol is used as a building block in organic synthesis for the production of pharmaceuticals and other fine chemicals. Its chiral nature and reactivity make it an important compound in the development of chiral drugs and enantioselective processes.
Used in Chemical Industry:
(1R,2S')-α-(pyrrolidin-2-yl)benzyl alcohol is utilized as a key intermediate in the synthesis of various chemical compounds, contributing to the versatility and innovation in the chemical industry.

Upstream product

• 5700-74-3 (S)-N-(ethoxycarbonyl)proline 
• 1147426-64-9 (1S,2R)-2-(hydroxy(phenyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 100-58-3 phenylmagnesium bromide 
• 344-25-2 D-Prolin 
• 1314228-04-0 (R)-methyl 1-tosylpyrrolidine-2-carboxylate 
• 134513-04-5 [1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol 
• 1033699-62-5 (R)-1-tritylpyrrolidine-2-carbaldehyde 
• 1033699-79-4 C₂₄H₂₅NO 
• 1033699-77-2 C₂₅H₂₅NO₂ 
• 43041-12-9 methyl (2R)-pyrrolidine-2-carboxylate 
• 885462-61-3 (2R,1'S)-N-[(S)-2-(p-tolylsulfinyl)]-2-[(2-p-tolylsulfinylphenyl)triisopropylsilyloxymethyl]pyrrolidine 

Downstream Products

• 866219-00-3 (4R,5S)-oxazaphospholidine 
• 1147426-75-2 (1S,2R)-(1-benzylpyrrolidin-2-yl)phenylmethanol 
• 866219-07-0 2-chloro-1,3,2-oxazaphospholidine 

Relevant academic research and scientific papers

STEREOSELECTIVE SYNTHESIS OF PHOSPHOROTHIOATE OLIGORIBONUCLEOTIDES

The present invention relates to chiral phosphoramidites represented by formula (Ia) or formula (Ib) as novel monomers for the synthesis of stereodefined phosphorothioate MOE oligonucleotides. Furthermore, the present invention relates to a method for synthesizing stereodefined phosphorothioate MOE oligonucleotides using said novel chiral phosphoramidites.

Highly stereoselective syntheses of proline-derived vicinal amino alcohols through grignard addition onto N-tosylprolinal

A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

Mechanistic interrogation of the asymmetric lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine

A fundamental mechanistic study of the s-BuLi/chiral diamine-mediated lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine is reported. We show that lithiated thiopivalamides are configurationally unstable at -78 °C. Reaction then proceeds via a dynamic resolution of diastereomeric lithiated intermediates and this accounts for the variable sense and degree of asymmetric induction observed compared to N-Boc heterocycles.

Catalytic asymmetric synthesis of piperidines from pyrrolidine: Concisesynthesis of L-733,060

Catalytic asymmetric deprotonation-aldehyde trapping-ring expansion from a 5- to a 6-ring delivers a concise route to each stereoisomer of -hydroxy piperidines starting from W-Boc pyrrolidine. The methodology is utilized in a 5-step catalytic asymmetric synthesis of the neorokinin-1 receptor antagonist, (+)-L-733,060.

Quick access to optically pure 2-(1-hydroxybenzyl)piperidine and pyrrolidine

Optically pure 2-(1-hydroxybenzyl)piperidine and pyrrolidine were prepared by reaction of oxygenated 2-(p-tolylsulfinyl)benzyl carbanions with the appropriate chlorinated N-sulfinylimines followed by subsequent elimination of the sulfinyl groups. The main reaction is a tandem process involving nucleophilic addition of the sulfinylbenzyl carbanion to the C=N bond followed by intramolecular elimination of the chlorine by the resulting amide. The matched pair of the reagents (exhibiting the same configuration at their respective sulfinyl moieties) evolves with a complete control of the stereoselectivity at the two newly created chiral carbons. Georg Thieme Verlag Stuttgart.

Highly Stereospecific Arylation Of (S)-Proline and Complementary Highly Diastereoselective Reduction of the α-Amino Ketone. Asymmetric Synthesis of (1S,2'S)- and (1R,2'S)-Phenyl(2'-pyrrolidinyl)methanol

Both optically active threo- and erythro-phenyl(2'-pyrrolidinyl)methanol (93-100percent enantiomeric excess, 100percent diastereoisomeric excess) were synthesised from (S)-proline by a stereospecific arylation and the subsequent complementary diastereoselective reduction of the α-amino ketone.