88763-76-2

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Aminopiperidine-2-one is used as a key intermediate for the synthesis of various pharmaceuticals, particularly those targeting central nervous system disorders and neurological diseases. Its chiral nature allows for the production of specific enantiomers with desired therapeutic effects.
Used in the Synthesis of Antiemetic Agents:
(R)-3-Aminopiperidine-2-one is used as a building block in the synthesis of ondansetron and ramosetron, which are antiemetic and antinausea agents. These compounds are crucial in managing nausea and vomiting associated with various conditions and treatments, such as chemotherapy and pregnancy.
Used in the Synthesis of Biologically Active Compounds:
(R)-3-Aminopiperidine-2-one is utilized in the synthesis of other biologically active compounds, further expanding its applications in the pharmaceutical industry. Its versatility as a chemical intermediate makes it an essential component in the development of new drugs and therapeutic agents.

InChI:InChI=1/C5H10N2O.ClH/c6-4-2-1-3-7-5(4)8;/h4H,1-3,6H2,(H,7,8);1H/t4-;/m1./s1

Upstream product

• 81084-75-5 ornithine methyl ester 
• 1069-31-4 L-ornithine hydochloride 
• 3184-13-2 L-ornithine hydrochloride 
• 16682-12-5 D-ornithine hydrochloride 
• 70-26-8 D-ornithine 
• 1892-22-4 3-aminopiperidin-2-one 
• 1069-31-4 (R)-2,5-diaminopentanoic acid dihydrochloride 
• 70-26-8 D-Ornithin 
• 138377-80-7 3-aminopiperidin-2-one hydrochloride 
• 261522-14-9 ornithine methyl ester hydrochloride 
• 1069-31-4 DL-ornithine hydrochloride 
• 34294-79-6 (S)-(-)-3-aminopiperidin-2-one 

Downstream Products

• 70-26-8 2,5-diaminopentanoic acid 
• 3328-28-7 N-(2'-oxopiperidin-3'-yl)benzamide 
• 34294-79-6 (S)-(-)-3-aminopiperidin-2-one 
• 137585-21-8 2-(2,3-dimethoxystyryl)-4,5,6,7-tetrahydrothiazolo[5,4-b]pyridine 
• 99780-98-0 (+/-)-3-<(tert-butoxycarbonyl)amino>-2-piperidone 
• 221874-51-7 (3R)-3-[(tert -butoxycarbonyl)amino]-2-piperidone 
• 722499-65-2 (3R)-3-benzyloxycarbonylamino-2-piperidinone 
• 334618-23-4 3-(R)-aminopiperidine dihydrochloride 

Relevant academic research and scientific papers

Convenient synthesis of (R)-3-[(tert -Butoxycarbonyl)amino]piperidine and (R)-3-[(tert -Butoxycarbonyl)amino]azepane

(R)-3-[(tert -Butoxycarbonyl)amino]piperidine and (R)-3-[(tert -butoxycarbonyl)amino]azepane were prepared in two steps starting from d -ornithine and d -lysine, respectively. In the key step, N -Boc-protected 3-aminolactams were converted into imido esters by O-alkylation and then hydrogenated to amines, under mild conditions (5 bar H 2, room temperature) and without isolation, over a standard hydrogenation catalyst (5% Pt/C).

PROTAC-mediated crosstalk between E3 ligases

Small-molecule heterobifunctional degraders can effectively control protein levels and are useful research tools. We assembled proteolysis targeting chimeras (PROTACs) from a cereblon (CRBN) and a von-Hippel-Lindau (VHL) ligase ligand and demonstrated a PROTAC-induced heterodimerization of the two E3 ligases leading to unidirectional and efficient degradation of CRBN.

Substituted xanthine compound and its preparation and use (by machine translation)

The invention discloses substituted xanthine compounds, a preparation method and applications thereof, and specifically relates to compounds represented by the formula (I), stereo isomers and pharmaceutically acceptable salts thereof, wherein the R1 and R2 are defined in the description. The invention also relates to a pharmaceutical composition containing the compounds, an application of the pharmaceutical composition in preparation of drugs for treating diseases or symptoms caused by high activity of DPP-IV or overexpression of DPP-IV, and a method using the pharmaceutical composition to treat related diseases. The provided compounds can effectively inhibit the activity of DPP-IV.

Synthesis of bengamide E analogues and their cytotoxic activity

A series of bengamide E analogues were prepared from the corresponding polyketide chain and amino acids via amide coupling reactions. Opening of the polyketide chain lactone ring with α-aminolactams was successfully achieved under microwave irradiation in the presence of sodium 2-ethyl hexanoate. A cytotoxic activity evaluation against a panel of cancer cell lines (KB, HepG-2, Lu-1, MCF-7, HL-60 and Hela) indicated that the 2′R analogues were generally more cytotoxic than the 2′S analogues. Additionally, several analogues exhibited selective inhibition against various cancer cell lines: compounds 32a and 32b selectively inhibited MCF-7 cells, while 33b and 35b were more sensitive toward Lu-1 and HepG-2, respectively. Notably, some of the synthetic analogues possess cytotoxic activities with IC50 values less than 1?μM.

Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues

Rhodium(II) acetate catalyzed domino reactions of bis-diazo compounds afford epoxy- and epithio-bridged heterocycle-fused quinolizinone systems in a stereoselective manner. The presence of an acceptor diazo functionality leads to a selective intermolecular X-H insertion reaction in a chemoselective manner, and the acceptor/acceptor diazo functionality subsequently participates in the formation of isomünchnone/thioisomünchnone 1,3-dipoles followed by intramolecular cycloaddition in a diastereoselective manner. This domino reaction is capable of constructing epoxy- and epithio-bridged heterocycle-fused quinolizinone ring systems with four stereogenic centers. The Bronsted acid induced reactions of oxa-bridged tricyclic compounds furnish ring-opened alcohol products in a regioselective manner.

Highly enantioselective synthesis of non-natural aliphatic α-amino acids via asymmetric hydrogenation

By employing a rhodium-Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and Linagliptin in the DPP-4 inhibitor class was also developed.

NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

The present invention provides a novel compound having a superior activity as an ERR-alpha modulator and useful as an agent for the prophylaxis or treatment of ERR-alpha associated diseases. The present invention relates to a compound represented by the formula (1) wherein each symbol is as defined in the specification, or a salt thereof

Resolution of α-aminolactams by inclusion complexation with chiral host compounds

3-Aminopiperidin-2-one and α-amino-ε-caprolactam were efficiently resolved by inclusion complexation with a chiral host compound, (R,R)-(-)-trans-4,5-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane . The amino substituent on the lactam ring was found to play an important role in efficient chiral recognition in the inclusion crystals.

Amino-caprolactam derivatives as γ-secretase inhibitors

A series of amino-caprolactam sulfonamides were developed from a screening hit. Compounds with good in vitro and in vivo γ-secretase activity are reported.

PREPARATION OF (R)-3-AMINOPIPERIDINE DIHYDROCHLORIDE

Described herein are methods for making chiral derivatives of 3-aminopiperidine, including the production of such derivatives in quantities exceeding 1 kilogram. The chiral 3-aminopiperidine derivatives include (R) -3-aminopiperidine derivatives which may be used to synthesize inhibitors of Dipeptidyl Peptidase IV. (R) -3-Aminopiperidine dihydrochloride is prepared by reducing (R) -3-aminopiperidin-2-one hydrochloride with lithium aluminum hydride. The preparation of (R) -3-aminopiperidin-2-one hydrochloride starting from (R) -methyl-2, 5-diaminopentanoate dihydrochloride or (R) -2, 5-diaminopentanoic acid hydrochloride is also described.