42538-31-8

Basic information

• Product Name: (S)-3-aminopiperidin-2-one Hydrochloride
• Synonyms: (S)-3-AMino-2-piperidone Hydrochloride;Ornithine-1,5-LactaM HCl;(S)-3-AMino-2-piperidone hydrochloride 95%;(3S)-3-Amino-2-piperidinone Hydrochloride;(S)-3-aminopiperidin-2-one Hydrochloride;3-(S)-AMINO-PIPERIDIN-2-ONE HYDROCHLORIDE;Aspartic acid Impurity B;42538-31-8
• CAS NO: 42538-31-8
• Molecular Formula: C₅H₁₀N₂O*ClH
• Molecular Weight: 150.61
• Product Categories: CHIRAL CHEMICALS
• Mol File: 42538-31-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: (S)-3-aminopiperidin-2-one Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-aminopiperidin-2-one Hydrochloride(42538-31-8)
• EPA Substance Registry System: (S)-3-aminopiperidin-2-one Hydrochloride(42538-31-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 42538-31-8(Hazardous Substances Data)

Usage

Uses

(S)-3-Amino-2-piperidone hydrochloride can be used as a building block for the synthesis of 5-hydroxy-2-[(3S)-2-oxo-3-piperidinyl]-1H-isoindole-1,3(2H)-dione by reacting with 4-hydroxyphthalic anhydride. It is also used to prepare eukaryotic signaling peptide glorin and its synthetic analog glorinamide.

Upstream product

• 78397-39-4 Boc-Orn-OMe 
• 3184-13-2 L-ornithine hydrochloride 
• 92235-39-7 3(S)-<(butoxycarbonyl)amino>-2-oxopiperidine 
• 40216-82-8 methyl (S)-2,5-diaminopentanoate dihydrochloride 
• 2480-95-7 methyl (S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanoate 

Downstream Products

• 54012-73-6 (S)-piperidin-3-amine 
• 869810-56-0 (S)-5-hydroxy-2-(2-oxo-piperidin-3-yl)-isoindole-1,3-dione 
• 95582-17-5 (S)-3-[[(phenylmethoxy)carbonyl]amino]-2-oxopiperidine 
• 1352127-81-1 (S)-3-fluoro-N-(2-oxopiperidin-3-yl)benzamide 
• 1352143-88-4 (S)-4-fluoro-N-(2-oxopiperidin-3-yl)benzenesulfonamide 
• 1067658-81-4 tert-butyl methyl((S)-piperid-2-one-3-ylamino-(R)-oxo-3-phenylpropan-2-yl)carbamate 
• 1067658-69-8 tert-butyl methyl((S)-piperid-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)carbamate 
• 672883-83-9 (3S)-3-(3-cyclopentyloxy-4-difluoromethoxyphenylcarboxamido)-2-oxohexahydropyridine 
• 114200-46-3 3(S)-amino>-2-oxopiperidine 
• 672883-82-8 (3S)-3-(3-cyclopentyloxy-4-methoxyphenylcarboxamido)-2-oxohexahydropyridine 
• 672883-86-2 (3S)-3-(3-cyclopentyloxy-4-methoxyphenylcarboxamido)-2-oxo-1-phenylhexahydro-pyridine 
• 672883-85-1 (3S)-3-[3,4-di(difluoromethoxy)phenylcarboxamido]-2-oxohexahydropyridine 
• 672883-84-0 (3S)-3-(3-cyclopropylmethyloxy-4-difluoromethoxyphenylcarboxamido)-2-oxohexahydro-pyridine 

Relevant articles and documents

Versatile synthesis of the signaling peptide glorin

We present a versatile synthesis of the eukaryotic signaling peptide glorin as well as glorinamide, a synthetic analog. The ability of these compounds to activate glorin-induced genes in the social amoeba Polysphondylium pallidum was evaluated by quantita

Development of a large-scale synthesis of sulphostin, a dipeptidyl peptidase IV inhibitor

For the progress of the in vivo study on sulphostin, a dipeptidyl peptidase IV inhibitor, its large-scale synthetic method was investigated. The optical resolution of (3S,RSP)-1-amino(sulfoamino)phosphinyl-3- benzyloxycarbonylamino-2-piperidinone, which was the most difficult step in the previous method, was simplified by using fractional crystallization. The use of 2 mol equiv of (1S,2R)-(+)-2-amino-1,2-diphenylethanol for optical resolution gave desired diastereomer 15 in good yield as a less soluble salt. In the present synthetic method, there were no requirements for purification using column chromatography, reaction at cryogenic temperature, and treatment using the haloalkane solvents. The total yield of the new method was 4.6%, which was an improvement of approximately 2-fold compared to the method reported previously.

Three-step synthesis of (R)- and (S)-Thalidomides from ornithine

Three-step synthesis of enantiomerically pure thalidomide is described. D-Ornithine (2) reacted with thionyl chloride in methanol followed by treatment with triethylamine to give the (R)-3-amino-piperidin-2-one hydrochloride (3) in good yield. Protection of amino moiety by the use of N-carboethoxyphtalimide in DMSO furnished (R)-N-phtaloylpiperidin-2-one (4) as colorless crystals. Finally, the oxidation using a catalytic amount of RuO2 in the presence of excess sodium metaperiodate in a two-phase system gave (R)-thalidomide (1) in good yield without racemization. (S)-Thalidomide (1) was also synthesized from L-ornithine (2) in good overall yield. Since all the intermediates to thalidomide are easily recrystallized, the present method can be performed on a large scale without purification by column chromatography.