142374-19-4

Basic information

• Product Name: 4-(2-oxoethyl)piperidine-1-carboxylic acid,tert-butyl ester
• Synonyms: 1-(tert-butyloxycarbonyl)-piperidine-4-acetaldehyde;tert-Butyl 4-(formylmethyl)piperidine-1-carboxylate;tert-Butyl 4-(2-oxoethyl);n-boc-4-piperidineacetaldehyde;1-PIPERIDINE CARBOXYLIC ACID, 4-(2-OXOETHYL)-1,1-D;1-Boc-4-(2-oxo-ethyl)piperidine;tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate;tert-butyl 4-(2-oxoethyl)piperidin-1-carboxylate
• CAS NO: 142374-19-4
• Molecular Formula: C₁₂H₂₁NO₃
• Molecular Weight: 227.31
• Product Categories: pharmacetical
• Mol File: 142374-19-4.mol
• Article Data: 53

Chemical Properties

• Melting Point: 38-42 °C
• Boiling Point: 318.1°Cat760mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.035g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.467
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: -1.62±0.40(Predicted)
• CAS DataBase Reference: 4-(2-oxoethyl)piperidine-1-carboxylic acid,tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-oxoethyl)piperidine-1-carboxylic acid,tert-butyl ester(142374-19-4)
• EPA Substance Registry System: 4-(2-oxoethyl)piperidine-1-carboxylic acid,tert-butyl ester(142374-19-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 142374-19-4(Hazardous Substances Data)

Usage

Description

4-(2-oxoethyl)piperidine-1-carboxylic acid, tert-butyl ester is an organic compound with the molecular formula C12H21NO3. It is a derivative of piperidine, a heterocyclic compound with a six-membered ring containing one nitrogen atom. The tert-butyl ester group is attached to the carboxylic acid functionality, which provides additional reactivity and synthetic utility.

Uses

Used in Pharmaceutical Industry:
4-(2-oxoethyl)piperidine-1-carboxylic acid, tert-butyl ester is used as a key intermediate for the synthesis of various pharmaceutical compounds, such as Pim-1 inhibitors. Pim-1 inhibitors are a class of drugs that target the Pim-1 protein, which is involved in cell proliferation and survival, and has been implicated in various cancers.
Used in the Synthesis of GPR119 Agonists:
4-(2-oxoethyl)piperidine-1-carboxylic acid, tert-butyl ester is also used as a reactant in the synthesis of selective GPR119 agonists. GPR119 is a G-protein coupled receptor that plays a role in glucose homeostasis and has been identified as a potential target for the treatment of type II diabetes.
Used in Organic Synthesis:
4-(2-oxoethyl)piperidine-1-carboxylic acid,tert-butyl ester serves as a versatile reactant for various organic synthesis processes, including α-arylation, enantioselective α-benzylation, and enantioselective α-trifluoromethylation of aldehydes. These reactions are important for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C12H21NO3/c1-12(2,3)16-11(15)13-7-4-10(5-8-13)6-9-14/h9-10H,4-8H2,1-3H3

Upstream product

• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 137076-22-3 tert butyl 4-formylpiperidine-1-carboxylate 
• 622-26-4 4-(2-Hydroxyethyl)piperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 502609-58-7 tert-butyl 4-(2-oxoethylidene)piperidine-1-carboxylate 
• 60-29-7 diethyl ether 
• 79-37-8 oxalyl dichloride 
• 89151-44-0 4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester 
• 28356-58-3 pyridine-4-acetic acid 
• 51052-78-9 4-piperidinylacetic acid 
• 157688-46-5 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid 
• 6622-91-9 2-(pyridine-4-yl)acetic acid hydrochloride 
• 135716-08-4 tert-butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate 

Downstream Products

• 339525-17-6 1-(o-iodobenzoyl)-4-[3-(trimethylsilyl)prop-2-ynyl]piperidine 
• 339525-21-2 1-(o-iodobenzoyl)-4-[4-(trimethylsilyl)but-3-ynyl]piperidine 
• 146144-48-1 N-<<3(R)-(-)-<2-(piperidin-4-yl)ethyl>-2-oxopiperidin-1-yl>acetyl>-3(R)-methyl-β-alanine 
• 756873-25-3 tert-butyl 4-[2-hydroxy-2-(4-methoxy-2,6-dimethyl-phenyl)-ethyl]-piperidine-1-carboxylate 
• 142355-84-8 4-{4-[4-((S)-2-Benzyloxycarbonylamino-2-carboxy-ethyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 142373-59-9 4-(4-{4-[(S)-2-(Butane-1-sulfonylamino)-2-carboxy-ethyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists: Modifications of the arylpropylpiperidine side chains

The 4-(3-phenylprop-1-yl)piperidine moiety of the 1,3,4-trisubstituted pyrrolidine CCR5 antagonist 1 was modified with electron deficient aromatics as well as replacement of the benzylic methylene with sulfones, gem-difluoromethylenes and alcohols in an effort to balance the antiviral potency with reasonable pharmacokinetics.

Exploiting Synergistic Catalysis for an Ambient Temperature Photocycloaddition to Pyrazoles

Sydnone-based cycloaddition reactions are a versatile platform for pyrazole synthesis, however they operate under harsh conditions (high temperature and long reaction times). Herein we report a strategy that addresses this limitation utilizing the synergistic combination of organocatalysis and visible-light photocatalysis. This new approach proceeds under ambient conditions and with excellent levels of regiocontrol. Mechanistic studies suggest that photoactivation of sydnones, rather than enamines, is key to the successful implementation of this process.

6-bromo-3-(piperidine-4-yl)imidazo[1,2-a]pyridine preparation method

The invention relates to a 6-bromo-3-(piperidine-4-yl)imidazo[1,2-a]pyridine preparation method. A purpose of the present invention is mainly to solve the technical problem that no suitable industrialsynthesis method exists in the prior art. According to the technical scheme, the method comprises five steps, and comprises: generating a compound 2 from a compound 1 and Boc2O in chloroform under the action of triethylamine; adding dichloromethane, oxalyl chloride and dimethyl sulfoxide into the compound 2, and oxidizing to obtain a compound 3; carrying out a reaction on the compound 3 and a bromination reagent phenyltrimethylammonium tribromide (PTAB) in tetrahydrofuran to obtain a compound 4; carrying out a reaction on the compound 4 and 2-amino-5-bromopyridine in ethyl alcohol to obtain acompound 5; and finally obtaining a compound 6 from the compound 5 under the action of ethyl acetate hydrochloride. According to the present invention, the obtained compound can be used as the intermediate or product for synthesis of a plurality of drugs.