1-PIPERIDINECARBOXYLIC ACID,4-[(HYDROXYIMINO)METHYL]-,1,1-DIMETHYLETHYL ESTER

Base Information

• Chemical Name: 1-PIPERIDINECARBOXYLIC ACID,4-[(HYDROXYIMINO)METHYL]-,1,1-DIMETHYLETHYL ESTER
• CAS No.: 190446-85-6
• Molecular Formula: C11H20N2O3
• Molecular Weight: 228.28800
• Hs Code.: 2933399090
• Mol file: 190446-85-6.mol

Synonyms:1-Boc-4-((Hydroxyimino)methyl)piperidine;tert-butyl 4-[(hydroxylimino)methyl]piperidine-1-carboxylate;4-N(tert-butoxycarbonyl)piperidinecarboxaldehyde oxime;tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate;

Chemical Property of 1-PIPERIDINECARBOXYLIC ACID,4-[(HYDROXYIMINO)METHYL]-,1,1-DIMETHYLETHYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 343.583oC at 760 mmHg
• PKA: 11.27±0.28(Predicted)
• Flash Point: 161.593oC
• PSA: 62.13000
• Density: 1.138g/cm3
• LogP: 2.03140

Purity/Quality:

99% ^*data from raw suppliers

1,1-DimethylethylEster4-[(Hydroxyimino)methyl]-1-piperidinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-PIPERIDINECARBOXYLIC ACID,4-[(HYDROXYIMINO)METHYL]-,1,1-DIMETHYLETHYL ESTER

There total 4 articles about 1-PIPERIDINECARBOXYLIC ACID,4-[(HYDROXYIMINO)METHYL]-,1,1-DIMETHYLETHYL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

tert butyl 4-formylpiperidine-1-carboxylate (137076-22-3) → tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate (190446-85-6)

Guidance literature:

With hydroxylamine hydrochloride; sodium carbonate; In methanol; water; at 0 - 15 ℃; Cooling with ice;

Reference yield:

tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate (123855-51-6) → tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate (190446-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide

2: hydroxylamine hydrochloride; sodium hydrogencarbonate

With hydroxylamine hydrochloride; sulfur trioxide pyridine complex; sodium hydrogencarbonate; triethylamine; In dimethyl sulfoxide;

DOI:10.1039/c6ra02365g

Reference yield:

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid (84358-13-4,174286-31-8) → tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate (190446-85-6)

Guidance literature:

Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran

2: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide

3: hydroxylamine hydrochloride; sodium hydrogencarbonate

With sodium tetrahydroborate; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; sulfur trioxide pyridine complex; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1039/c6ra02365g

upstream raw materials:

tert butyl 4-formylpiperidine-1-carboxylate

tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

Downstream raw materials:

(S)-2-hydroxy-1-(4-(5-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)propan-1-one

2-hydroxy-1-(4-(5-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone

(R)-2-hydroxy-1-(4-(5-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)propan-1-one

tert-butyl 4-(5-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate

Refernces

• 1、 Aicher, Thomas D.,Baer, Brian R.,Boyd, Steven A.,Chicarelli, Mark D.,Condroski, Kevin R.,DeWolf, Walter E.,Fischer, John,Frank, Michele,Hingorani, Gary P.,Hinklin, Ronald J.,Lee, Patrice A.,Neitzel, Nickolas A.,Pratt, Scott A.,Singh, Ajay,Sullivan, Francis X.,Turner, Timothy,Voegtli, Walter C.,Wallace, Eli M.,Williams, Lance. "Discovery and preclinical development of AR453588 as an anti-diabetic glucokinase activator". supporting information. . Retrieved 2019/12/24.
• 2、 Chalyk, Bohdan A.,Kandaurova, Inna Y.,Hrebeniuk, Kateryna V.,Manoilenko, Olga V.,Kulik, Irene B.,Iminov, Rustam T.,Kubyshkin, Vladimir,Tverdokhlebov, Anton V.,Ablialimov, Osman K.,Mykhailiuk, Pavel K.. "A base promoted multigram synthesis of aminoisoxazoles: Valuable building blocks for drug discovery and peptidomimetics". . p. 25713 - 25723. Retrieved 2016/03/25.