172603-05-3

Basic information

• Product Name: 3-N-Boc-aminopiperidine
• Synonyms: CARBAMIC ACID, 3-PIPERIDINYL-, 1,1-DIMETHYLETHYL ESTER;(+/-)-3-N-BOC-AMINO-PIPERIDINE;3-N-BOC-AMINO PIPERIDINE;3-(TERT-BUTOXYCARBONYLAMINO)PIPERIDINE;3-BOC-AMINOPIPERIDINE;3-AMINOPIPERIDINE, 3-BOC PROTECTED;PIPERIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER;TERT-BUTYL PIPERIDIN-3-YLCARBAMATE
• CAS NO: 172603-05-3
• Molecular Formula: C10H20N2O2
• Molecular Weight: 200.28
• EINECS: 1592732-453-0
• Product Categories: N-BOC;pharmacetical;Piperidine;API intermediates;Piperidine Series;Piperidines;Amines;Pyrans, Piperidines & Piperazines
• Mol File: 172603-05-3.mol

Chemical Properties

• Melting Point: 102-108°C
• Boiling Point: 304.8 °C at 760 mmHg
• Flash Point: 138.2 °C
• Appearance: White/Crystalline Powder
• Density: 1.02 g/cm³
• Vapor Pressure: 0.000854mmHg at 25°C
• Refractive Index: 1.479
• Storage Temp.: 2-8°C
• Solubility: DMSO, Methanol
• PKA: 12.37±0.20(Predicted)
• CAS DataBase Reference: 3-N-Boc-aminopiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-N-Boc-aminopiperidine(172603-05-3)
• EPA Substance Registry System: 3-N-Boc-aminopiperidine(172603-05-3)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-36/37/39-61-60
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 172603-05-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-N-Boc-aminopiperidine is used as a key intermediate in the synthesis of highly selective spleen tyrosine kinase inhibitors. These inhibitors play a crucial role in modulating the immune response and have potential applications in the treatment of autoimmune diseases and inflammatory conditions.
3-N-Boc-aminopiperidine is also used as a synthetic building block for the development of a potent NHE1 inhibitor. This inhibitor displays cardioprotective effects and has potential applications in the treatment of heart-related conditions, such as ischemia-reperfusion injury and heart failure.

InChI:InChI=1/C10H20N2O2/c1-10(2,3)14-9(13)12-8-5-4-6-11-7-8/h8,11H,4-7H2,1-3H3,(H,12,13)

Upstream product

• 92235-39-7 3(S)-<(butoxycarbonyl)amino>-2-oxopiperidine 
• 6893-26-1 D-Glutamic acid 
• 861658-15-3 1,5-dimethyl (2R)-2-[[(tert-butoxy)carbonyl]amino]pentanedioate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 397246-12-7 tert-butyl N-[(2R)-1,5-dihydroxypentan-2-yl]carbamate 
• 34404-28-9 N-[(1,1-dimethylethoxy)carbonyl]-D-glutamic acid 
• 16682-12-5 D-ornithine hydrochloride 
• 221874-51-7 (3R)-3-[(tert -butoxycarbonyl)amino]-2-piperidone 
• 88763-76-2 (R)-(+)-3-Amino-2-piperidinon 
• 168466-84-0 (3R)-1-benzyl-3-aminopiperidine 
• 245529-50-4 (R)-1-benzylpiperidine-3-carboxylic acid ethyl ester 
• 163343-71-3 (R)-piperidine-3-carboxylic acid ethyl ester*l-tartaric acid 
• 71962-74-8 Ethyl nipecotate 
• 1050446-94-0 C₁₄H₁₈N₂O₃ 

Downstream Products

• 1431978-01-6 {1-[6-(4-Hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperidin-3-yl}-carbamic acid tert-butyl ester 
• 889948-89-4 tert-butyl (1-(4-aminophenyl)piperidin-3-yl)carbamate 
• 1361323-46-7 tert-butyl (S)-1-((S)-1-((S)-1-(2-methoxyphenethyl)piperidin-3-ylamino)-3,3-dimethyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate 
• 1361322-66-8 (S)-N-((S)-1-(2-methoxyphenethyl)piperidin-3-yl)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanamide 
• 1361323-47-8 tert-butyl (S)-1-((S)-1-((S)-1-(3-methoxyphenethyl)piperidin-3-ylamino)-3,3-dimethyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate 
• 1361322-67-9 (S)-N-((S)-1-(3-methoxyphenethyl)piperidin-3-yl)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanamide 
• 1361323-48-9 tert-butyl (S)-1-((S)-1-((S)-1-(4-methoxyphenethyl)piperidin-3-ylamino)-3,3-dimethyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate 
• 1361322-68-0 (S)-N-((S)-1-(4-methoxyphenethyl)piperidin-3-yl)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanamide 
• 1361322-69-1 (S)-N-((S)-1-(4-chlorophenethyl)piperidin-3-yl)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanamide 
• 1361322-70-4 (S)-N-((S)-1-(4-bromophenethyl)piperidin-3-yl)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanamide 

Relevant articles and documents

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).

Synthesis method of chiral 3-aminopiperidine and derivatives of 3-aminopiperidine

The invention relates to a synthesis method of chiral 3-aminopiperidine and derivatives of 3-aminopiperidine. According to the synthesis method, R (or S)-piperidine-3-ethyl formate-L (or D)-tartrate is subjected to a hydrazinolysis reaction after being subjected to benzyl protection, and R or S-1-benzyl-3-aminopiperidine is obtained through azidation and Curtius rearrangement. R or S-1-benzyl-3-aminopiperidine is subjected to debenzylation, R or S-3-aminopiperidine can be obtained, R or S-1-benzyl-3-aminopiperidine is subjected to 3-t-butyloxycarboryl protection and debenzylation in sequence,R or S-(3-t-butyloxycarborylamino) piperidine can be obtained, and corresponding salts of R or S-3-aminopiperidine can be obtained through hydrolyzing deprotection of R or S-(3-t-butyloxycarborylamino) piperidine under the acidic condition. The synthesis method of chiral 3-aminopiperidine and the derivatives of 3-aminopiperidine is low in cost, facilitates industrialization and has high optical purity.

Synthetic process of anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride

The invention relates to a synthetic process of an anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride. The synthetic process comprises the steps: using inexpensive L-glutamic acid as a starting material, and performing esterification, amino protection, reduction, hydroxyl protection, substitution, cyclization and removal of protecting groups for amino groups so as to obtainthe R-3-amino-piperidine dihydrochloride. Compared with the prior art, the synthetic process has cheap and easily available raw materials, good selectivity, good atomic economy, high total yield and mild reaction conditions, and is suitable for industrial production.

(R)- 3 - Boc - amino piperidine preparation method

The invention discloses a preparation method of (R)-3-Boc-aminopiperidine and relates to the technical field of preparation of piperidine heterocyclic compounds. The preparation method includes following steps: (1) with N-Cbz-3-piperidinecarboxylic acid as a raw material, performing chiral resolution with R-phenylethylamine to obtain a compound I; (2) performing an acid-amide condensation reaction to the compound I and ammonia gas to obtain a compound II; (3) performing a Hofmann degradation reaction to the compound II to obtain a compound III; (4) performing protection to the compound III with di-tert-butyl dicarbonate to obtain a compound IV; and (5) performing a hydrogenation and Cbz-removal reaction to the compound IV to prepare the (R)-3-Boc-aminopiperidine. The method is mild in reaction conditions, is safe and reliable, is excellent in process stability, is low in energy consumption, is high in yield, is green and environment-protective and is suitable for industrial production.

(R) - 3-amino-piperidine dihydrochloride preparation method

The invention discloses a method for preparing (R)-3-amino piperidine hydrochloride. D-glutamic acid is taken as a starting material, and the (R)-3-amino piperidine hydrochloride is obtained by reaction in the following five steps: (1) hydroxyl esterification and amido Boc protection; (2) ester reduction; (3) hydroxyl activation; (4) cyclization; (5) amino Boc removal protection. The preparation method disclosed by the invention is short in synthetic route and low in cost, and industrial production can be achieved.

Amino-protected (R) - 3-amino-piperidine preparation method

The invention discloses a preparation method of amino protection (R)-3-amino piperidine, and the preparation method comprises the following steps: (1) in the presence of a first solvent or absence of a solvent, reacting a compound of formula V with benzylamine to obtain a compound of formula VI; (2) in the presence of a second solvent, performing catalytic hydrogenation of the compound of formula VI to remove benzyl to obtain the amino protection (R)-3-amino piperidine. According to the method, the defects of use of expensive metal catalysts and use of high-pressure hydrogenation and various splitting for synthesis of a chiral amino piperidine ring can be avoided, at the same time, the synthetic route is short, the process is simple, the yield is high, and the method is suitable for industrial mass production.

Discovery of imidazopyridazines as potent Pim-1/2 kinase inhibitors

High levels of Pim expression have been implicated in several hematopoietic and solid tumor cancers, suggesting that inhibition of Pim signaling could provide patients with therapeutic benefit. Herein, we describe our progress towards this goal using a screening hit (rac-1) as a starting point. Modification of the indazole ring resulted in the discovery of a series of imidazopyridazine-based Pim inhibitors exemplified by compound 22m, which was found to be a subnanomolar inhibitor of the Pim-1 and Pim-2 isoforms (IC50values of 0.024?nM and 0.095?nM, respectively) and to potently inhibit the phosphorylation of BAD in a cell line that expresses high levels of all Pim isoforms, KMS-12-BM (IC50?=?28?nM). Profiling of Pim-1 and Pim-2 expression levels in a panel of multiple myeloma cell lines and correlation of these data with the potency of compound 22m in a proliferation assay suggests that Pim-2 inhibition would be advantageous for this indication.

MANUFACTURING METHOD FOR A PIPERIDINE-3-YLCARBAMATE COMPOUND AND OPTICAL RESOLUTION METHOD THEREFOR

Provided is a manufacturing method for a piperidin-3-ylcarbamate compound in which a pyridin-3-ylcarbamate compound and hydrogen are brought into contact in the presence of a palladium catalyst.

TETRAHYDRO-IMIDAZOY1,5-A¨PYRAZINE DERIVATIVES, PREPARATION METHODS AND MEDICAL USES THEREOF

Tetrahydro-imidazo[1,5-a]pyrazine derivatives of formula ( I ), their preparation methods, pharmaceutical compositions containing the derivatives and uses thereof as medicaments, especially as dipeptidyl peptidase IV inhibitor, wherein the substituents of formula ( I ) are defined as same as the description.

STEREOSELECTIVE SYNTHESIS OF PIPERIDINE DERIVATIVES

This invention relates to dialdehyde or dinitrile compounds, which are useful for stereoselective synthesis of piperidine, pyrrolidine, and azepane derivatives.