118811-03-3

Basic information

• Product Name: 2-(2-HYDROXY-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: BOC-2-(2-PIPERIDYL)ETHANOL;2-(2-HYDROXYETHYL)-1-BOC-PIPERIDINE;2-(2-HYDROXY-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-BOC-2-(2-HYDROXY-ETHYL)-PIPERIDINE;(+/-)-N-BOC-PIPERIDINE-2-ETHANOL;N-BOC-2-HYDROXYETHYLPIPERIDINE;N-BOC-2-(2-HYDROXYETHYL)PIPERIDINE;N-BOC-2-PIPERIDIN-2-YL-ETHANOL
• CAS NO: 118811-03-3
• Molecular Formula: C₁₂H₂₃NO₃
• Molecular Weight: 229.32
• Product Categories: pharmacetical
• Mol File: 118811-03-3.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 100-110 °C/0.3 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.032 g/mL at 25 °C
• Vapor Pressure: 6.34E-06mmHg at 25°C
• Refractive Index: n20/D 1.472
• PKA: 15.15±0.10(Predicted)
• CAS DataBase Reference: 2-(2-HYDROXY-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-HYDROXY-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(118811-03-3)
• EPA Substance Registry System: 2-(2-HYDROXY-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(118811-03-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 24/25-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 118811-03-3(Hazardous Substances Data)

Usage

Uses

Reactant for synthesis of:Vasopressin1b receptor antagonistsCXCR4 antagonists as anti-HIV agentsCoumarin-based inhibitors of inducible nitric oxide synthaseSelective thrombin inhibitorsReactant for: N-directed hydroboration for synthesis of amino alcoholsEnantioselective synthesis of sedamine and allosedamine

InChI:InChI=1/C11H22N2O3/c1-11(2,3)16-10(15)13-6-5-12-8-9(13)4-7-14/h9,12,14H,4-8H2,1-3H3

Upstream product

• 1484-84-0 2(RS)-(2-hydroxyethyl)piperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 133633-94-0 (±)-hexahydro-3H-pyrido[1,2-c][1,2,3]oxathiazine 1,1-dioxide 
• 98303-20-9 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 183859-36-1 methyl (+/-)-N-(tert-butyloxycarbonyl)piperidin-2-ylacetate 
• 3040-44-6 1-piperidinoethanol 

Downstream Products

• 199861-72-8 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 199942-79-5 2-{2-[3-(3-bromophenyl)-7-chloro-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 199861-86-4 2-{2-[6-allyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 210564-52-6 t-butyl 2-(2-bromoethyl)piperidine-1-carboxylate 
• 791-28-6 Triphenylphosphine oxide 
• 158550-57-3 (+/-)-2-[(4-benzylphenoxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Formal synthesis of (±)-sedamine through gold(I)-catalyzed intramolecular dehydrative amination of sulfamate esters tethered to allylic alcohols

A concise formal synthesis of (±)-sedamine has been accomplished. The synthesis is straightforward and demonstrates high efficiency. Key steps involve gold(I)-catalyzed cyclization of sulfamate esters tethered to allylic alcohols, sulfamate N-alkylation, and ring-closing metathesis.

Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate

α-Trifluoromethyl azocanes are accessible from 2-(trifluoropropan-2-ol) piperidines by metal-free ring-expansion involving a bicyclic azetidinium intermediate. The opening of the azetidinium intermediate was achieved by various nucleophiles (amines, alcoholates, carboxylates, phosphonates, halides and pseudo-halides) with an excellent regio- diastereo- and enantioselectivity and in good yields. The relative configuration of the piperidines and azocanes were assigned and the deprotected azocanes offer opportunities for further derivatization.

Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis

The neuroleptic drug thioridazine has been recently repositioned as possible anti-tubercular drug. Thioridazine showed anti-tubercular activity against drug resistant mycobacteria but it is endowed with adverse side effects. A small library of thioridazine derivatives has been designed through the replacement of the piperidine and phenothiazine moieties, with the aim to improve the anti-tubercular activity and to reduce the cytotoxic effects. Among the resulting compounds, the indole derivative 12e showed an antimycobacterial activity significantly better than thioridazine and a cytotoxicity 15-fold lower.