625471-18-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Amino-1-N-Boc-piperidine is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with specific biological activities.
Used in Enzyme Inhibition Research:
(S)-3-Amino-1-N-Boc-piperidine is used to prepare selective noncovalent inhibitors of the bacterial cysteine protease IdeS. This application is significant in the study of enzyme function and the development of novel therapeutic agents targeting specific proteases implicated in various diseases.
Used in Chiral Chemistry:
The product obtained by the reductive elimination reaction with ethylglyoxalte is used as a reference compound, which is employed to determine the absolute configuration of the two enantiomers. This application is essential in chiral chemistry, where understanding the stereochemistry of compounds is crucial for their reactivity, biological activity, and potential applications.

Upstream product

• 1271240-70-0 (S)-3-azido-1-N-tert-butyloxycarbonylpiperidine 
• 1374353-02-2 1,1-dimethylethyl (3S)-3-azidopiperidine-1-carboxylate 
• 62414-68-0 (3R)-piperidin-3-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 53912-80-4 (S)-N-benzylprolinol 
• 113304-84-0 N-benzyl-(S)-proline methyl ester 
• 91599-79-0 (S)-1-N-benzyl-3-hydroxypiperidine 
• 344-25-2 D-Prolin 
• 143900-43-0 tert-butyl (3R)-3-hydroxypiperidine-1-carboxylate 
• 98977-36-7 3-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 75-31-0 isopropylamine 

Downstream Products

• 960116-31-8 C₂₂H₂₆ClN₅O₂ 
• 953772-09-3 (S)-tert-butyl 3-(6-methoxybenzo[d]thiazol-2-ylamino)piperidine-1-carboxylate 
• 1217636-04-8 C₁₂H₂₄N₂O₂ 
• 915230-71-6 (S)-3-[3-(4-fluoro-phenyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester 
• 870220-96-5 (S)-N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-amine 
• 1207852-39-8 (3S)-tert-butyl 3-(6-(imidazo[1,2-a]pyridin-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate 
• 1261301-88-5 C₂₅H₂₉ClN₄O₄S 
• 1261302-03-7 C₁₈H₂₂N₄O₂S 
• 1271240-99-3 (S)-1-N-tert-butyloxycarbonyl-3-[(5-amino-6-chloropyrimidin-4-yl)amino]piperidine 
• 1271240-81-3 1-((S)-1-N-tert-butyloxycarbonylpiperidin-3-yl)-3-((E)-3-ethoxyacryloyl)urea 
• 1271241-02-1 (S)-1-N-tert-butyloxycarbonyl-3-[(2,5-diamino-6-chloropyrimidin-4-yl)amino]piperidine 
• 1271240-90-4 (S)-3-(uracil-1-yl)piperidine 
• 1271241-05-4 (S)-1-N-tert-butyloxycarbonyl-3-(6-chloropurin-9-yl)piperidine 

Relevant academic research and scientific papers

A Rapid Selection Procedure for Simple Commercial Implementation of ω-Transaminase Reactions

A stepwise selection procedure is presented to quickly evaluate whether a given ω-transaminase reaction is suitable for a so-called "simple" scale-up for fast industrial implementation. Here "simple" is defined as a system without the need for extensive process development or specialized equipment. The procedure may be used when investment in intensive process development cannot be justified or when rapid execution is paramount, for applications such as small singular batches. The three-step evaluation procedure consists of: (1) thermodynamic assessment, (2) biocatalyst activity screening, and (3) determination of product inhibition. The method is exemplified with experimental work focused on two products: 1-(4-bromophenyl)ethylamine and (S)-(+)-3-amino-1-Boc-piperidine, synthesized from their corresponding pro-chiral ketones each with two alternative amine donors, propan-2-amine, and 1-phenylethylamine. Each step of the method has a threshold value, which must be surpassed to allow "simple" implementation, helping select suitable combinations of substrates, enzymes, and donors. One reaction pair, 1-Boc-3-piperidone with propan-2-amine, met the criteria of the three-step selection procedure and was subsequently run at 25 mL scale synthesizing (S)-(+)-3-amino-1-Boc-piperidine at concentrations up to 75 g/L. However, the highest product yield (70%) was obtained at a lower substrate concentration of 50 g/L.

Asymmetric synthesis of a high added value chiral amine using immobilized ω-transaminases

Chiral N-heterocyclic molecules and in particular compounds with an amino functional group such as 3-aminopiperidine are valuable intermediates for the production of a large number of bioactive compounds with pharmacological properties. In this paper, the synthesis of both enantiomers of 3-amino-1-Boc-piperidine by amination of the prochiral precursor 1-Boc-3-piperidone using immobilized ω-transaminases (TAs-IMB), isopropylamine as amine donor and pyridoxal-5’-phosphate (PLP) as cofactor is described. Compared to other methods, the present approach affords the target compound in just one step with high yield and high enantiomeric excess starting from a commercial substrate. The reaction was carried out by using different commercially available immobilized enzymes, evaluating the catalytic activity and the enantioselectivity under different experimental conditions. Re-use of the most efficient enzyme was performed both in batch and in a semi-continuous system. The selected biocatalyst showed good stability under the reaction conditions providing consistent results in terms of conversion and enantiomeric excess after several cycles. The reported results may be of practical interest in view of the development of this sustainable approach to an industrial scale.

The identification and use of robust transaminases from a domestic drain metagenome

Transaminases remain one of the most promising biocatalysts for use in chiral amine synthesis, however their industrial implementation has been hampered by their general instability towards, for example, high amine donor concentrations and organic solvent content. Herein we describe the identification, cloning and screening of 29 novel transaminases from a household drain metagenome. The most promising enzymes were fully characterised and the effects of pH, temperature, amine donor concentration and co-solvent determined. Several enzymes demonstrated good substrate tolerance as well as an unprecedented robustness for a wild-type transaminase. One enzyme in particular readily accepted IPA as an amine donor giving the same conversion with 2-50 equivalents, as well as being tolerant to a number of co-solvents, and operational in up to 50% DMSO-a characteristic as yet unobserved in a wild-type transaminase. This work highlights the value of using metagenomics for biocatalyst discovery from niche environments, and here has led to the identification of one of the most robust native transaminases described to date, with respect to IPA and DMSO tolerance.

The synthesis of piperidine nucleoside analogs - A comparison of several methods to access the introduction of nucleobases

This work deals with the synthesis of piperidine and hydroxypiperidine analogs of nucleosides. Starting from commercially available 3-hydroxypiperidine, proline or 4-hydroxyproline, a series of piperidine derivatives of both purine and pyrimidine nucleobases was prepared. Various methods of nucleobase attachment were evaluated. The prepared compounds were tested for cytostatic, antibacterial, and antiviral properties but no significant activity was found.

TREATMENT OF LEARNING DISABILITIES AND MOTOR SKILLS DISORDER WITH NOREPINEPHRINE REUPTAKE INHIBITORS

Provided are methods and medicaments for treating a learning disability or a Motor Skills Disorder, comprising administering to a patient in need of such treatment an effective amount of a selective norepinephrine reuptake inhibitor.

3-AMINOPIPERIDINES AND 3-AMINOQUINUCLIDINES AS INHIBITORS OF MONOAMINE UPTAKE

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, which are useful for the inhibition of the uptake of one or more physiologically active monoamines (serotonin, norepinephrine, and dopamine).

TREATMENT OF PERVASIVE DEVELOPMENTAL DISORDERS WITH NOREPINEPHRINE REUPTAKE INHIBITORS

Provided are methods and medicaments for treating a Pervasive Developmental Disorder, comprising administering to a patient in need of such treatment an effective amount of a selective norepinephrine reuptake inhibitor.

TREATMENT OF HOT FLASHES, IMPULSE CONTROL DISORDERS AND PERSONALITY CHANGE DUE TO A GENERAL MEDICAL CONDITION

Selective norepinephrine reuptake inhibitors are useful for the prevention or treatment of hot flashes, vasomotor symptoms, impulse control disorders or personality change due to a general medical condition.