228244-04-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-1-Boc-2-cyanopyrrolidine is used as a key intermediate in the synthesis of prolyl oligopeptidase (POP) inhibitors. These inhibitors are designed to target and modulate the activity of POP, an enzyme involved in various biological processes, including the regulation of neuropeptides and the degradation of proteins. The development of POP inhibitors has significant potential in the treatment of neurological disorders and other diseases.
Used in the Design of DPP-4 Inhibitors:
(S)-1-Boc-2-cyanopyrrolidine is also used as a reagent in the design of potent and selective inhibitors of dipeptidyl peptidase-4 (DPP-4). DPP-4 is an enzyme that plays a crucial role in the regulation of glucose homeostasis by inactivating incretin hormones, which stimulate insulin secretion. Inhibitors of DPP-4 have emerged as an attractive class of antidiabetic agents due to their ability to improve glycemic control with a favorable pharmacokinetic profile. The use of (S)-1-Boc-2-cyanopyrrolidine in the design of these inhibitors allows for the development of more effective and selective drugs with improved therapeutic potential.

Upstream product

• 75-05-8 acetonitrile 

Downstream Products

• 207557-35-5 (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile 
• 274901-16-5 vildagliptin 
• 204387-53-1 (2S)-pyrrolidine-2-carbonitrile 
• 1597528-87-4 C₁₈H₂₄ClN₃O₄ 
• 1597528-85-2 (S)-2-[5-(3-chloro-2-methylphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1597529-15-1 5-(3-chloro-2-methylphenyl)-3-(S)-pyrrolidin-2-yl-[1,2,4]oxadiazole 
• 1597522-78-5 {(S)-2-[5-(3-chloro-2-methylphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone 
• 1609019-85-3 4-(4-iodophenyl)butanoyl-L-prolyl-2(S)-cyanopyrrolidine 
• 1609019-86-4 4-(4-trimethylstannylphenyl)butanoyl-L-prolyl-2(S)-cyanopyrrolidine 
• 662722-99-8 (R)-2-((S)-1-tert-Butoxycarbonyl-pyrrolidin-2-yl)-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 117175-41-4 tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate 
• 872341-97-4 [(S)-1-Biphenyl-4-ylmethyl-2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Process Development of the Copper(II)-Catalyzed Dehydration of a Chiral Aldoxime and Rational Selection of the Co-Substrate

The access towards chiral nitriles remains crucial in the synthesis of several pharmaceuticals. One approach is based on metal-catalyzed dehydration of chiral aldoximes, which are generated from chiral pool-derived aldehydes as substrates, and the use of a cheap and readily available nitrile as co-substrate and water acceptor. Dehydration of N-acyl α-amino aldoximes such as N-Boc-l-prolinal oxime catalyzed by copper(II) acetate provides access to the corresponding N-acyl α-amino nitriles, which are substructures of the pharmaceuticals Vildagliptin and Saxagliptin. In this work, a detailed investigation of the formation of the amide as a by-product at higher substrate loadings is performed. The amide formation depends on the electronic properties of the nitrile co-substrate. We could identify an acceptor nitrile which completely suppressed amide formation at high substrate loadings of 0.5 m even when being used with only 2 equivalents. In detail, utilization of trichloroacetonitrile as such an acceptor nitrile enabled the synthesis of N-Boc-cyanopyrrolidine in a high yield of 92 % and with full retention of the absolute configuration.

Process Development of a Copper(II)-Catalyzed Dehydration of an N -Acyl Prolinal Oxime: Cascade Process and Application at an Elevated Lab Scale

Chiral N-acyl amino nitriles are important structural motifs in several pharmaceuticals such as Vildagliptin or Saxagliptin. Cyanidefree access to such nitriles is provided by a copper-catalyzed dehydration of oximes, which are readily available by condensation of chiral aldehydes resulting from the chiral pool with hydroxylamine. The application in a cascade process without the need for intermediate purification as well as a demonstrated scalability show the robustness of this methodology.