100858-34-2

Basic information

• Product Name: R-1-CBZ-3-Hydroxy-piperidine
• Synonyms: R-1-CBZ-3-Hydroxy-piperidine;(R)-1-Cbz-3-hydroxy-piper...;(R)-Benzyl 3-hydroxypiperidine-1-carboxylate;benzyl (3R)-3-hydroxypiperidine-1-carboxylate
• CAS NO: 100858-34-2
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.27898
• Mol File: 100858-34-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 384.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.220±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.72±0.20(Predicted)
• CAS DataBase Reference: R-1-CBZ-3-Hydroxy-piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: R-1-CBZ-3-Hydroxy-piperidine(100858-34-2)
• EPA Substance Registry System: R-1-CBZ-3-Hydroxy-piperidine(100858-34-2)

Safety Data

• Hazardous Substances Data: 100858-34-2(Hazardous Substances Data)

Usage

General Description

R-1-CBZ-3-Hydroxy-piperidine is a chemical compound frequently used as an intermediate in the synthesis of pharmaceuticals. The prefix "R" indicates its configuration, which means it has a specific geometric arrangement in space. The "CBZ" is an abbreviation for carboxybenzyl, denoting the type of protection group in the molecule that shields certain functionalities from reactions. The "3-Hydroxy" indicates the compound contains a hydroxyl group (-OH) located at the third carbon in the piperidine ring - a common structure in organic chemistry comprising five carbon atoms and one nitrogen atom. This chemical is typically used in laboratory or industrial settings.

Upstream product

• 62414-68-0 (3R)-piperidin-3-ol 
• 501-53-1 benzyl chloroformate 
• 61995-20-8 N-(benzyloxycarbonyl)-3-piperidone 
• 110-86-1 pyridine 
• 79328-85-1 N-benzyloxycarbonyl-1,2-dihydropyridine 
• 188660-19-7 (R)-N-Carbobenzoxy-3-hydroxy-1,2,3,4-tetrahydropyridine 
• 95798-22-4 3-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 6859-99-0 3-hydroxypiperazine 
• 164472-76-8 (R)-(+)-5-bromo-2-hydroxypentanenitrile 
• 174621-92-2 benzyl 3-acetoxypiperidine-1-carboxyate 
• 66207-23-6 1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine 

Downstream Products

• 227614-36-0 (3R)-(aminooxy)-1-(carbobenzyloxy)piperidine 

Relevant articles and documents

Enantioenriched N-(2-Chloroalkyl)-3-acetoxypiperidines as Potential Cholinotoxic Agents. Synthesis and Preliminary Evidence for Spirocyclic Aziridinium Formation.

The syntheses of six enantioenriched analogs representing cyclic forms of acetylcholine are reported. (S)- and (R)-N-(2-chloroethyl)-3-acetoxypiperidine and (R,R)-, (R,S)-, (S,R)-, and (S,S)-N-(2-chloropropyl)-3-acetoxypiperidine have been synthesized from (R)- or (S)-3-hydroxypiperidine in five steps. (R)- and (S)-3-hydroxypiperidine were accessed via parallel stereospecific routes from d- and l-glutamic acid, and through fractional recrystallization of diastereomeric tartranilic acid salts. (S)-N-(2-Chloroethyl)-3-acetoxypiperidine was reacted with silver perchlorate to form a spirocyclic aziridinium analog of acetylcholine as evidenced by a characteristic 1H NMR shift for the aziridinium methylene groups.

Stereo-complementary bioreduction of saturated N-heterocyclic ketones

The asymmetric bioreduction of several saturated N-heterocyclic ketones is demonstrated in a stereo-complementary fashion using the ketoreductases READH and ChKRED20 for the production of (S)- and (R)-alcohols, respectively. The reaction accepts substrates with a five-, six- or seven-membered ring, and exhibits excellent stereoselectivity when using 2-propanol as both the ultimate reducing agent and cosolvent, achieve >99% ee in the majority of cases for both enantiomers.

Chemoenzymatic synthesis of azacycloalkan-3-ols

Optically active ω-bromocyanohydrins are easily synthesized through an enantioselective (R)-oxynitrilase-catalyzed reaction from their corresponding ω-bromoaldehydes. These cyanohydrins are starting materials for the preparation of medium size nitrogen heterocycles. The reduction of (R)-(+)-5- bromo-2-hydroxypentanenitrile affords, in one-pot, piperidin-3-ol. Azepan-3- ol and azocan-3-ol are readily obtained from their corresponding cyanohydrins in high enantiomeric excesses.