942142-74-7

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxyMethyl]-, 1,1-diMethylethyl ester, (3R)-
• Synonyms: 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxyMethyl]-, 1,1-diMethylethyl ester, (3R)-;tert-Butyl (R)-3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate
• CAS NO: 942142-74-7
• Molecular Formula: C₁₇H₂₄ClNO₃
• Molecular Weight: 325.83036
• Mol File: 942142-74-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 432.6°C at 760 mmHg
• Flash Point: 215.4°C
• Appearance: /
• Density: 1.192g/cm³
• Vapor Pressure: 2.99E-08mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxyMethyl]-, 1,1-diMethylethyl ester, (3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxyMethyl]-, 1,1-diMethylethyl ester, (3R)-(942142-74-7)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxyMethyl]-, 1,1-diMethylethyl ester, (3R)-(942142-74-7)

Safety Data

• Hazardous Substances Data: 942142-74-7(Hazardous Substances Data)

Usage

General Description

1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester, (3R)- is a chemical compound that is commonly known as tadalafil. It is a phosphodiesterase 5 (PDE5) inhibitor used to treat erectile dysfunction and symptoms of benign prostatic hyperplasia. Tadalafil works by relaxing the smooth muscles in the blood vessels, allowing for increased blood flow to certain areas of the body. It is available in tablet form and is typically taken orally as needed, with or without food. Tadalafil is a prescription medication, and its use should be supervised by a healthcare professional to ensure safety and effectiveness.

InChI:InChI=1/C17H24ClNO3/c1-17(2,3)22-16(21)19-9-5-7-13(11-19)15(20)12-6-4-8-14(18)10-12/h4,6,8,10,13,15,20H,5,7,9,11H2,1-3H3/t13-,15+/m1/s1

Upstream product

• 163438-09-3 (R)-1-Boc-nipecotic acid 
• 884510-86-5 (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate 
• 884512-09-8 (R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate 

Downstream Products

• 1240123-86-7 (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2,2-dimethoxypropoxy)methyl)piperidine-1-carboxylate 
• 942145-03-1 (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylate 
• 942145-04-2 (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methylsulfonyloxy)ethoxy)methyl)piperidine-1-carboxylate 
• 942145-05-3 (R)-tert-butyl 3-((R)-(2-azidoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate 
• 942142-78-1 (R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate 
• 942142-79-2 (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate 
• 942145-39-3 methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate 
• 1013631-24-7 methyl (2-((R)-(3-chlorophenyl)((R)-1-(((S)-1-(methylamino)-3-((S)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamoyl)piperidin-3-yl)methoxy)ethyl)carbamate trifluoroacetate 
• 1013937-63-7 methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate 
• 942142-81-6 methyl 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate 
• 942142-76-9 (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate 
• 942144-91-4 (R)-tert-butyl 3-((R)-(3-chlorophenyl)(3-cyanopropoxy)methyl)piperidine-1-carboxylate 

Relevant articles and documents

Discovery of VTP-27999, an alkyl amine renin inhibitor with potential for clinical utility

Structure guided optimization of a series of nonpeptidic alkyl amine renin inhibitors allowed the rational incorporation of additional polar functionality. Replacement of the cyclohexylmethyl group occupying the S1 pocket with a (R)-(tetrahydropyran-3-yl)

PROCESS FOR THE ASYMMETRIC REDUCTION OF 3-BENZOYLPIPERIDINES

Disclosed is a process for the asymmetric preparation of a phenyl(3-piperidinyl)methanol represented by Formula (I): wherein R is an optionally substituted phenyl and E is an amine protecting group.

Design and optimization of renin inhibitors: Orally bioavailable alkyl amines

Structure-based drug design led to the identification of a novel class of potent, low MW alkylamine renin inhibitors. Oral administration of lead compound 21l, with MW of 508 and IC50 of 0.47 nM, caused a sustained reduction in mean arterial bl