114715-39-8

Usage

Uses

Used in Agrochemical Industry:
(R)-(-)-1-Benzyl-3-aminopyrrolidine is used as a key intermediate for the synthesis of various agrochemicals, such as pesticides and fertilizers, to enhance crop protection and yield.
Used in Pharmaceutical Industry:
(R)-(-)-1-Benzyl-3-aminopyrrolidine is utilized as a crucial building block in the development of new pharmaceutical compounds, contributing to the creation of innovative drugs for various medical conditions.
Used in Dye Industry:
(R)-(-)-1-Benzyl-3-aminopyrrolidine is employed as an essential intermediate in the production of dyes, playing a vital role in the synthesis of colorants for various applications, including textiles, plastics, and printing inks.

InChI:InChI=1/C11H16N2.ClH/c12-11-6-7-13(9-11)8-10-4-2-1-3-5-10;/h1-5,11H,6-9,12H2;1H/t11-;/m1./s1

Upstream product

• 66832-28-8 1-benzyl-3-(hydroxyimino)pyrrolidine 
• 368429-69-0 4-amino 1-benzylpyrrolidin-2-one 
• 51535-00-3 methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 116143-03-4 (3R)-3-azido-1-(phenylmethyl)pyrrolidine 
• 118354-71-5 (S)-methanesulfonic acid 1-benzylpyrrolidin-3-yl ester 
• 18471-40-4 1-Benzyl-3-aminopyrrolidine 
• 77-78-1 dimethyl sulfate 
• 131878-23-4 (3R)-1-benzyl-3-[(tert-butoxycarbonyl)(methyl)amino]pyrrolidine 
• 1227263-77-5 (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol 
• 116183-79-0 (3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine 
• 6159-55-3 (+)-vasicinol 

Downstream Products

• 96901-81-4 5-bromo-2,4-dimethoxy-N-(1-benzyl-3-pyrrolidinyl)benzamide 
• 61694-71-1 N-(1-benzyl-3-pyrrolidinyl)-4-amino-5-chloro-2-methoxybenzamide 
• 73328-60-6 N-(1-Benzyl-3-pyrrolidinyl)-5-chloro-2-methoxy-4-methylaminobenzamide 
• 61694-77-7 N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-dimethylamino-2-methoxybenzamide 
• 78775-22-1 N-(1-Benzyl-pyrrolidin-3-yl)-5-chloro-4-ethylamino-2-methoxy-benzamide 
• 78784-41-5 N-(1-Benzyl-pyrrolidin-3-yl)-5-chloro-4-formylamino-2-methoxy-benzamide 
• 78775-26-5 4-Acetylamino-N-(1-benzyl-pyrrolidin-3-yl)-5-chloro-2-methoxy-benzamide 
• 78775-24-3 4-Benzylamino-N-(1-benzyl-pyrrolidin-3-yl)-5-chloro-2-methoxy-benzamide 
• 72412-41-0 2-Amino-4-methoxy-pyrimidine-5-carboxylic acid (1-benzyl-pyrrolidin-3-yl)-amide; compound with oxalic acid 
• 336191-80-1 Ethyl 3-[(1-benzyltetrahydro-1H-3-pyrrolyl)amino]-3-oxopropanoate 
• 212192-46-6 N-(1-benzyl-pyrrolidin-3-yl)-4-iodo-benzamide 

Relevant academic research and scientific papers

Synthesis method of 3-aminopyrrolidine dihydrochloride

The invention discloses a synthetic method of 3-aminopyrrolidine dihydrochloride. The synthetic method comprises the following steps: preparing benzyl-(3-ethoxy-3-alkenyl)-(1-vinyl ethoxy methyl) amine liquid; preparation of a 1-benzyl-3-pyrrolidone solution; preparation of a 1-benzyl-3-aminopyrrolidine solution; preparing a 1-benzyl-3-aminopyrrolidine salt; preparing a 3-aminopyrrolidine solution; the yield and purity of the 3-aminopyrrolidine dihydrochloride are improved by controlling the activity of the reaction main materials of each part in a segmented manner and carrying out a directional hydrogenation manner.

Development of the Late-Phase Manufacturing Process of ZPL389: Control of Process Impurities by Enhanced Process Knowledge

The development of the late-phase manufacturing process of the drug candidate ZPL389 and the strategies for the control of impurities are outlined in detail. Selective salt formation at several stages was pivotal to controlling the process impurities. The extensive optimization of the N-methylation of a Boc-protected amine with dimethyl sulfate and of a nucleophilic aromatic substitution without the use of metal catalysts led to a robust, scalable process. The process was demonstrated on a >100 kg scale. Overall, improved drug substance quality, higher yield, and reduction of the process mass intensity were achieved.

Discovery and Biological Evaluation of N-Methyl-pyrrolo[2,3- b]pyridine-5-carboxamide Derivatives as JAK1-Selective Inhibitors

Janus kinase 1 (JAK1) plays a key role in most cytokine-mediated inflammatory and autoimmune responses through JAK/STAT signaling; thus, JAK1 inhibition is a promising therapeutic strategy for several diseases. Analysis of the binding modes of current JAK inhibitors to JAK isoforms allowed the design of N-alkyl-substituted 1-H-pyrrolo[2,3-b] pyridine carboxamide as a JAK1-selective scaffold, and the synthesis of various methyl amide derivatives provided 4-((cis-1-(4-chlorobenzyl)-2-methylpiperidin-4-yl)amino)-N-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (31g) as a potent JAK1-selective inhibitor. In particular, the (S,S)-enantiomer of 31g (38a) exhibited excellent potency for JAK1 and selectivity over JAK2, JAK3, and TYK2. On investigating the effect of 31g on hepatic fibrosis, it was found that it reduces the proliferation and fibrogenic gene expression of TGF-β-induced hepatic stellate cells (HSCs). Specifically, 31g significantly inhibited TGF-β-induced migration of HSCs at 0.25 μM in wound-healing assays.

Preparation method of ceftobiprole intermediate (R)-1-benzyl-3-aminopyrrolidine

The invention discloses a preparation method of a ceftobiprole intermediate, namely (R)-1-benzyl-3-aminopyrrolidine. The preparation method specifically comprises the following steps: with D-asparticacid as an initial raw material, carrying out amino protection, esterification, reduction, bromination cyclization and 3-amino protection removal successively to obtain (R)-1-benzyl-3-aminopyrrolidine. According to the method, the defects that raw materials for preparing (R)-1-benzyl-3-aminopyrrolidine are expensive, high temperature and high pressure are needed, precious metal is used for catalysis and the like in the prior art are overcome. All the materials used in the invention are cheap and easily available, so cost is low; and reactions can be carried out at normal temperature, so energyconsumption is low, industrial production is facilitated, and pollution is small.

HETEROARYL COMPOUNDS AND THEIR USE AS MER INHIBITORS

Compounds of formula (I) [Formula should be inserted here] and a pharmaceutically acceptable salt thereof, wherein A, R1, R2, R3, R4, R5, R6, R7, R24, X, L, n and p are as defined in the specification, are useful for treating or preventing Mer tyrosine kinase receptor modulated disease or conditions. Also described are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.

Exploring Derivatives of Quinazoline Alkaloid l-Vasicine as Cap Groups in the Design and Biological Mechanistic Evaluation of Novel Antitumor Histone Deacetylase Inhibitors

l-Vasicine is a quinazoline alkaloid with an electron dense ring and additional functionalities in its structure. Employing target oriented synthesis (TOS) based on in silico studies, molecules with significant docking scores containing different derivatives of l-vasicine as caps were synthesized. Interestingly, one molecule, i.e., 4a, which contained 3-hyroxypyrrolidine as a cap group and a six carbon long aliphatic chain as a linker was found to inhibit HDACs. 4a showed more specificity toward class I HDAC isoforms. Also 4a was found to be less cytotoxic toward normal cell lines as compared to cancer cell lines. 4a inhibited cancer cell growth and induced cell death by various mechanisms. However, 4a was found to induce cell death independent of ROS generation, and unlike many natural product based HDAC inhibitors, 4a was found to be nontoxic under in vivo conditions. Importantly, we for the first time report the possibility of using a 3-hydroxypyrrolidine cap for the synthesis of HDAC inhibitors with good potency.

METHOD FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-NITROGENATED COMPOUND

Aiming at production of an optically active 3-amino nitrogen-containing compound which is useful as an intermediate in synthesis of medicines and pesticides, in particular, an optically active 1-protected-3-aminopyrrolidine derivative, from an inexpensive and readily available raw material by a process which is efficient and can be practiced industrially, an optically active 3-amino nitrogen-containing compound is produced by performing a reaction of an optically active 3-substituted nitrogen-containing compound with ammonia, methylamine, ethylamine or dimethylamine in the presence of water. In addition, a 1-protected-3-aminopyrrolidine derivative is produced by performing a reaction of an optically active 1-protected-3-(sulfonyloxy)pyrrolidine derivative with ammonia, methylamine, ethylamine, or dimethylamine in the presence of methanol, ethanol, n-propanol, or isopropanol under a pressure of less than 30 barr.

A protection strategy substantially enhances rate and enantioselectivity in ω-transaminase-catalyzed kinetic resolutions

The kinetic resolution of 3-aminopyrrolidine (3AP) and 3-aminopiperidine (3APi) with ω-transaminases was facilitated by the application of a protecting group concept. 1-N-Cbz-protected 3-aminopyrrolidine could be resolved with >99% ee at 50% conversion, the resolution of 1-N-Boc-3-aminopiperidine yielded 96% ee at 55% conversion. The reaction rate was up to 50-fold higher by using protected substrates. Most importantly, enantioselectivity increased remarkably after carbamate protection compared to the unprotected substrates (86 vs. 99% ee). Surprisingly, benzyl protection of 3AP had no influence on enantioselectivity. A possible explanation for this observation could be the different flexibility of the benzyl- or carbamate-protected 3AP as confirmed by NMR spectroscopy.

Chemo-enzymatic preparation of chiral 3-aminopyrrolidine derivatives

A new simple method for the enantioselective enzymatic hydrolysis of N-protected D-asparagine esters suitable for the use on the preparative scale is presented. Due to major obstacles observed under conventional reaction conditions - racemization of the retained ester and a strong enzyme inactivation - a comparatively low pH together with an organic co-solvent had to be employed. Under these conditions, nearly all tested proteases demonstrated good activity and excellent enantioselectivity giving access to the corresponding D-esters and L-asparagines in high optical purities (>95% ee) and good chemical yields (>40%). From the unnatural D-asparagine derivative, sequential cyclization, selective deprotection and reduction yielded efficiently benzyl protected (R)-3-aminopyrrolidine, a homo-chiral building block utilized in numerous drug candidates.

Method of heightening optical purity of 1-benzyl-3-aminopyrrolidine and salt for used therein

The present invention provides a method to improve the optical purity of 1-benzyl-3-aminopyrrolidine having a low optical purity using an inexpensive agent via a simple procedure. The present invention provides a method for improving the optical purity of 1-benzyl-3-aminopyrrolidine including the steps of converting 1-benzyl-3-aminopyrrolidine into an equimolar salt with an optically inactive acid, and recovering the salt as crystals. The present invention also provides a salt of 1-benzyl-3-aminopyrrolidine that is used in the method.