852324-29-9

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-Methyl-pyrrolidine-2-carbaldehyde is used as an intermediate in the synthesis of various medications for treating conditions such as hypertension, asthma, and allergies due to its higher biological activity in the (S)-enantiomer form.
Used in Fragrance and Flavor Industry:
(S)-1-Methyl-pyrrolidine-2-carbaldehyde is also utilized as a key ingredient in the manufacturing of fragrances and flavors, contributing to the development of new scents and tastes in the market.
Used in Research and Development:
(S)-1-Methyl-pyrrolidine-2-carbaldehyde is employed in research and development for its organic chemistry applications, furthering scientific understanding and innovation in the field.

Upstream product

• 34381-71-0 (S)-2-hydroxymethyl-1-methylpyrrolidine 
• 147-85-3 L-proline 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 88218-12-6 S-pyrrolidine-2-carbaldehyde 
• 74-88-4 methyl iodide 
• 69610-41-9 Boc-L-Pro-H 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 27957-91-1 N-Methyl-L-proline Methyl Ester 

Downstream Products

• 639821-08-2 2,6-Bis-[1-((S)-1-methyl-pyrrolidin-2-yl)-meth-(E)-ylidene]-cyclohexanone 
• 181359-58-0 (7R,8R,8aS)-5-Oxo-8-phenylselanyl-octahydro-indolizine-7-carboxylic acid ethyl ester 
• 1269662-75-0 (E)-N-[4-[(3-chloro-4-fluorophenyl)amino]-7-ethoxyquinazolin-6-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]propan-2-enoylamine 
• 1269662-72-7 (E)-N-[4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]quinazolin-6-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]propan-2-enoylamine 
• 1269662-69-2 (E)-N-[4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-3-[(2S)-1-methylpyrrolidin-2-yl]propan-2-enoylamine 

Relevant academic research and scientific papers

Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form

Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.

Compound (E)-3-(1-methylpyrrolidine-2-yl)-acrylic hydrochloride and synthetic method

The invention discloses a compound (E)-3-(1-methylpyrrolidine-2-yl)-acrylic hydrochloride and a synthetic method. The compound is structurally as shown in a formula (I). The synthetic method of the compound comprises the following steps: using BOC-L-prolinol (or BOC-D-prolinol) as an initial material, and by oxidization, forming aldehyde; removing a BOC protective agent; then reacting with haloalkane; then by a Wittig reaction, synthesizing (S,E)-3-(1-methylpyrrolidine-2-yl)-ethyl acrylate; after hydrolysis, salifying to obtain (S,E)-3-(1-methylpyrrolidine-2-yl)-acrylic hydrochloride [or (R,E)-3-(1-methylpyrrolidine-2-yl)-acrylic hydrochloride]. The compound, as a medical intermediate, can be used for preparing quinazoline or quinolines medicine derivatives. The formula is shown in the description.

6-AMINO QUINAZOLINE OR 3-CYANO QUINOLINE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF

The present disclosure relates to 6-amino quinazoline or 3-cyano quinoline derivatives, preparation processes and pharmaceutical compositions containing them. Specifically, the present disclosure relates to novel 6-amino quinazoline or 3-cyano quinoline derivatives presented by formula (I), or its tautomer, enantiomer, diastereomer, racemate or pharmaceutically acceptable salts thereof, or metabolite, metabolic precursor or prodrug thereof, and the uses for treatment especially for protein kinase inhibitors, in which each substitute group of general formula (I) is as defined in the specification.

Synthesis of acyclic ketones by catalytic, bidirectional homologation of formaldehyde with nonstabilized diazoalkanes. Application of a chiral diazomethyl(pyrrolidine) in total syntheses of erythroxylon alkaloids

This work offers a catalytic approach to convergent ketone assembly based upon formal and tandem C-H insertion of diazoalkanes in the presence of limiting amounts of monomeric formaldehyde, which is easily generated as a gas by thermolysis of the inexpensive and abundant paraformaldehyde (～30 USD/kg). The method forms di-, tri-, and even tetrasubstituted acetones with high efficiency, and it has streamlined a synthesis of (-)-dihydrocuscohygrine in which the absolute stereochemistry of a proline-based starting material is preserved. Assisted by the advent of new protocols for hydrazone oxidation, we also provide full details on handling non-carbonyl-stabilized diazo compounds.

6-AMINO QUINAZOLINE OR 3-CYANO QUINOLINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL USES THEREOF

6-amino quinazoline or 3-cyano quinoline derivatives, preparation methods and pharmaceutical uses thereof are disclosed. Specifically, the present disclosure discloses novel 6-amino quinazoline or 3-cyano quinoline derivatives presented by general formula (I), or tautomers, enantiomers, diastereomers, racemates or pharmaceutically acceptable salts thereof, or metabolites, metabolic precursors or prodrugs thereof, and their uses as treatment agents especially as protein kinase inhibitors, in which each substitutent group of general formula (I) is as defined in the specification.

MELANOCORTIN RECEPTOR AGONISTS

The present invention relates a compound of formula 1, and pharmaceutically acceptable salt, hydrate, solvate, or isomer thereof effective as agonist of melanocortin receptor, and an agonistic composition of melanocortin receptor comprising the same as active ingredient.

Synthesis and α4β2 nicotinic affinity of 2- pyrrolidinylmethoxyimines and prolinal oxime ethers

Homochiral E and Z isomers of N-methylprolinal O-isopropyloxime and (1-methyl-2-pyrrolidinyl)methoxyimines were synthesized as candidate bioisosteres of nicotine and its isoxazolic analogue ABT 418. Two of them, namely (S)-2-isopropylideneaminooxymethyl- and (Z)-(S)-2- ethylideneaminooxymethyl-1-methylpyrrolidine, proved to bind at α4β2 nicotinic acetylcholine receptor with submicromolar affinity and remarkable selectivity over α7 and muscarinic receptors thus supporting the hypothesized bioisosteric relationship between their methyloxyimino group and the aromatic heterocycles of the reference ligands.

Rigidified acetylcholine mimics: Conformational requirements for binding to neuronal nicotinic receptors

Rigidified derivatives have been designed and synthesized assuming the g+t conformer of acetylcholine (N-C-C-O=+60°, C-C-O-C=180°) as active conformation for binding to cytisine sensitive neuronal nicotinic receptors. The SAR of the compounds evaluated, along with those of more flexible analogues, support the g+t conformer hypothesis and highlight the stringent steric limitation of this nicotinic receptor sub-type. Compound 3e has low μM affinity for cytisine sensitive nicotinic receptor binding sites while being selective with regard to the α-bungarotoxin sensitive subclass. We also report few compounds with μM affinity for the α-bungarotoxin sensitive subclass.

Diastereoselective Zwitterionic Aza-Claisen Rearrangement: Synthesis of Nine-Membered Ring Lactams and Transannular Ring Contraction

The zwitterionic aza-Claisen rearrangement of optically active 3-pyrrolidine acryl esters and various acid chlorides to generate optically active azoninones proceeds with high simple diastereoselectivity (internal asymmetric induction) and a complete 1,3-