1558-58-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-6-Methylpiperazin-2-one is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows it to be a key component in the development of new medications, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Agrochemical Production:
In the agrochemical industry, (S)-6-Methylpiperazin-2-one serves as an intermediate in the production of various agrochemicals. Its application in this field aids in the development of new compounds that can be used for pest control, crop protection, and other agricultural purposes, enhancing the efficiency and sustainability of farming practices.
Used in Fine Chemicals and Active Pharmaceutical Ingredients (API) Production:
(S)-6-Methylpiperazin-2-one is utilized as a building block in the creation of fine chemicals and active pharmaceutical ingredients. Its presence in this domain highlights its importance in the synthesis of complex and high-value chemical products, which are essential for various applications in the chemical and pharmaceutical industries.
Organic Synthesis:
(S)-6-Methylpiperazin-2-one is used as a versatile compound in organic synthesis, where it can be employed to create a wide range of chemical products. Its ability to form various chemical bonds and reactions makes it a valuable asset in the development of new organic compounds for different industries.

Upstream product

• 173173-75-6 (S)-1-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-piperidin-2-one 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 168827-91-6 (3-hydroxy-1-(S)-methyl-propyl)carbamic acid benzyl ester 
• 4775-98-8 δ-caprolactam 
• 13984-57-1 ethyl 5-oxohexanoate 
• 737760-86-0 (S)-4-isopropyl-3-(6-methylpyridin-2-yl)oxazolidin-2-one 
• 1413930-74-1 (S)-ethyl 5-(benzylamino)hex-2-ynoate 
• 170710-79-9 (3S,8aR)-8a-Methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 
• 3128-06-1 5-ketohexanoic acid 
• 709669-82-9 (2E,5S,αS)-ethyl 5-(N-benzyl-N-α-methylbenzylamino)hex-2-enoate 

Downstream Products

• 3197-42-0 (S)-2-methylpiperidine 
• 118173-33-4 (4S)-9a-(4-phenoxybutyl)-4-methylquinolizidine 

Relevant academic research and scientific papers

Resolution of α-aminolactams by inclusion complexation with chiral host compounds

3-Aminopiperidin-2-one and α-amino-ε-caprolactam were efficiently resolved by inclusion complexation with a chiral host compound, (R,R)-(-)-trans-4,5-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane . The amino substituent on the lactam ring was found to play an important role in efficient chiral recognition in the inclusion crystals.

Efficient production of enantiomerically pure chiral amines at concentrations of 50 g/L using transaminases

Two methods for the efficient (50 g/L) production of optically pure amines from their corresponding ketones using transaminases have been developed. The first method utilizes an ion-exchange resin for in situ product removal allowing the reaction to be carried out a substrate concentration of 50 g/L. The second approach relies upon conversion of the initially formed amine, via spontaneous cyclisation, to a noninhibitory product. Both methods have been demonstrated at 50 mL scale. (R)- and (S)-methylbenzylamine, and (R)- and (S)-6-methyl-2- piperidone have been produced in >90% isolated yield and >99% ee.

Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams

Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C?H and N?H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chemical complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work we report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.

Conversion of γ- and δ-Keto Esters into Optically Active Lactams. Transaminases in Cascade Processes

A one-pot two-step enzymatic strategy has been designed for the production of optically active γ- and δ-lactams in aqueous medium under mild conditions. The approach is based on the biotransamination of ethyl or methyl keto esters bearing different alkyl or aryl substitution patterns at α-position to the ketone functionality. In this manner, the keto esters were transformed into the corresponding amino esters with excellent conversions, which underwent spontaneous cyclisation in the reaction medium without addition of external reagents. Depending on the transaminase selectivity, both lactam enantiomers can be obtained, so initial enzyme screenings were performed using commercially available and made in house enzymes. Reaction conditions were optimised focusing on the substrate concentration, temperature and ratio of amine donor vs acceptor. Thus, ten γ- and δ-lactams were obtained in good to high isolated yields (70–90%) and excellent selectivities (94–99%) after one or two days at 30 or 45 °C. (Figure presented.).

A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline

Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline.

Asymmetric synthesis and applications of β-amino Weinreb amides: Asymmetric synthesis of (S)-coniine

Conjugate addition of lithium (S)-N-benzyl-N-a-methylbenzylamide to a range of α,β-unsaturated Weinreb amides proceeds with high levels of diastereoselectivity (>95% de). The β-amino Weinreb amide products may be transformed into β-amino ketones via reactions with Grignard reagents, while treatment with DIBAL-H furnishes β-amino aldehydes. Trapping of the aldehyde via Wadsworth-Emmons reaction and subsequent manipulation offers an efficient route to homochiral δ-amino acid derivatives and 2-substituted piperidines. The application of this methodology for the synthesis of (S)-coniine is demonstrated.

Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids. Applications in Wittig reactions and heterocycle synthesis

N-Z-γ-amino alcohols derived from nonracemic β-amino acids are smoothly oxidised by manganese dioxide in acetonitrile to afford aldehydes which can be trapped in situ in Wittig reactions with carbonyl-substituted phosphoranes. The application of this methodology to the synthesis of the alkaloids (S)-(+)-N-BOC-coniine, (S)-(-)-coniceine and a pipecoline precursor is described.

New highly enantioselective synthesis of 6-alkylpiperidin-2-ones and 2-substituted piperidines

A versatile and highly enantioselective approach to 2-substituted piperidines is described using phenylglycinol as chiral auxiliary.

Azapropellanes 5. Synthesis of chiral (non-racemic) 2-methyl azapropellanes

The preparation of S-(-)-6-methyl-2-piperidinone from S-alanine and R-(-)-5-methyl-2-pyrrolidinone from S-glutamic acid and their conversion into S-2-methyl-1-azoniatricyclo1.6>tetradecane (2a) and R-2-methyl-1-azoniatricyclo1.6>tridecane (2b) with enantiomeric excesses of 95 and 92percent respectively are described.The use of these compounds as phase-transfer catalysts did not lead to significant asymmetric induction.