22724-81-8

Basic information

• Product Name: L-NORVALINOL
• Synonyms: L-NORVALINOL;H-NVA-OL;(S)-(+)-2-AMINO-1-PENTANOL;(2S)-2-Amino-1-pentanol;(S)-(+)-2-Amino-1-pentanol,L-Norvalinol;(2S)-2-aMinopentan-1-ol;(S)-2-AMinopentan-1-ol;(2S)-2-AMino-1-pentanol HCl
• CAS NO: 22724-81-8
• Molecular Formula: C₅H₁₃NO
• Molecular Weight: 103.16
• Product Categories: Perindopril intermediate
• Mol File: 22724-81-8.mol

Chemical Properties

• Melting Point: 44-48 °C(lit.)
• Boiling Point: 195.6℃
• Flash Point: 214 °F
• Appearance: /
• Density: 0.915
• Vapor Pressure: 0.108mmHg at 25°C
• Refractive Index: 1.449
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 12.88±0.10(Predicted)
• CAS DataBase Reference: L-NORVALINOL(CAS DataBase Reference)
• NIST Chemistry Reference: L-NORVALINOL(22724-81-8)
• EPA Substance Registry System: L-NORVALINOL(22724-81-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 22724-81-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-NORVALINOL is used as a model compound for the study of estimation of dilution enthalpies of (R)-(-)-2-amino-1-pentanol in DMSO+H2O mixtures using isothermal titration calorimeter. This helps in understanding the thermodynamic properties and behavior of the compound, which is crucial for its pharmaceutical applications.
Used in Drug Development:
L-NORVALINOL is used as a substrate to prepare tricyclic heterocyclic compounds, which have potential as antagonists of corticotropin-releasing factor-1. These antagonists can be used in the development of drugs for the treatment of various stress-related disorders and anxiety.
Used in Antiviral Drug Synthesis:
L-NORVALINOL serves as an intermediate in one of the key synthetic steps for the preparation of the antiviral agent telaprevir. This highlights its importance in the development of antiviral drugs, which are essential in combating viral infections and diseases.

InChI:InChI=1/C5H13NO/c1-2-3-5(6)4-7/h5,7H,2-4,6H2,1H3/t5-/m0/s1

Upstream product

• 6600-40-4 L-Norvaline 
• 29582-96-5 L-norvaline methyl ester 
• 145842-50-8 benzyl N-[(1S)-1-(hydroxymethyl)butyl]carbamate 
• 56558-30-6 methyl L-norvalinate hydrochloride 
• 4146-04-7 DL-2-amino-1-pentanol 
• 64502-89-2 1-hydroxypentan-2-one 
• 6600-40-4 L-norvaline 

Downstream Products

• 112270-41-4 (S)-5-{7-[4-(4,5-Dihydro-4-propyl-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole 
• 62421-32-3 (2S)-2-[(p-tolylsulfonyl)amino]-1-[(p-tolylsulfonyl)oxy]pentane 
• 116611-57-5 tert-butyl [(1S)-1-(hydroxymethyl)butyl]carbamate 
• 170956-17-9 (S)-1-[(4-methylphenyl)sulfonyl]-2-propylaziridin 
• 152298-88-9 (2S)-N,N-dibenzyl-2-aminopentan-1-ol 
• 1004316-62-4 tert-butyl benzyl(1-hydroxypentan-2-yl)carbamate 
• 873196-91-9 (S)-N-benzyl-2-aminopentan-1-ol 
• 873196-93-1 (S)-N-benzyl-N-cyanomethyl-2-aminopentan-1-ol 
• 873196-96-4 (2E,4S)-4-(benzyl-cyanomethyl-amino)-hept-2-enoic acid ethyl ester 
• 873197-02-5 (2S,3S,4S)-(1-benzyl-2-cyano-4-propyl-azetidin-3-yl)-acetic acid ethyl ester 
• 873197-01-4 (2R,3S,4S)-(1-benzyl-2-cyano-4-propyl-azetidin-3-yl)-acetic acid ethyl ester 
• 378752-99-9 (S)-2-(N,N-Dibenzylamino)-pentanal 
• 599207-03-1 [(S)-1-((R)-1-Hydroxy-ethyl)-butyl]-carbamic acid tert-butyl ester 
• 260550-89-8 (S)-1-(benzofuran-2-yl)-2-propylaminopentane 

Relevant articles and documents

Data mining of amine dehydrogenases for the synthesis of enantiopure amino alcohols

Chiral amino alcohols are essential building blocks for the pharmaceutical industry, and are widely present in natural and synthetic bioactive compounds. Amine dehydrogenases (AmDHs) can asymmetrically reduce prochiral ketones with low-cost ammonia to chiral amines and water as by-products, using NAD(P)H as a cofactor under mild conditions, but hydroxy ketones with formation of chiral hydroxy amines have rarely been investigated. In this study, six new bacterial AmDHs derived from amino acid dehydrogenases (AADHs) were identified by data mining, and five out of the six enzymes were able to efficiently reduce 1-hydroxybutan-2-one (1a) to (S)-2-aminobutan-1-ol ((S)-2a) with 19-99% conversions and 99% ee. The five AmDHs were purified and biochemically characterized for reductive amination activity towards substrate 1a with the optimal pH at 8.5 or 9.0 and the optimal temperature at 45 °C, 50 °C or 55 °C, and provided reductive amination of a broad range of prochiral α-hydroxy ketones, and even of a model β-hydroxy ketone leading to β-hydroxy amine with 99% ee. Our study expands the toolbox of AmDHs in the synthesis of chiral amino alcohols.

Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases

Chiral vicinal amino alcohols are an important motif found in many biologically active molecules. In this study, biocatalytic reductive amination of α-hydroxy ketones with ammonia was investigated using engineered amine dehydrogenases (AmDHs) derived from the leucine amino acid dehydrogenase (AADH) from Lysinibacillus fusiformis. The AmDHs thus identified enabled the synthesis of (S)-configured vicinal amino alcohols from the corresponding α-hydroxy ketones in up to 99% conversions and >99% ee. One of the AmDH variants was used to prepare a key intermediate for the antituberculosis pharmaceutical ethambutol.

Palladium-N-heterocyclic carbene (NHC)-catalyzed asymmetric synthesis of indolines through regiodivergent C(sp3)-H activation: Scope and DFT study

Two bulky, chiral, monodentate N-heterocyclic carbene ligands were applied to palladium-catalyzed asymmetric C-H arylation to incorporate C(sp3)-H bond activation. Racemic mixtures of the carbamate starting materials underwent regiodivergent reactions to afford different trans-2,3- substituted indolines. Although this CAr-Calkyl coupling requires high temperatures (140-160°C), chiral induction is high. This regiodivergent reaction, when carried out with enantiopure starting materials, can lead to single structurally different enantiopure products, depending on the catalyst chirality. The C-H activation at a tertiary center was realized only in the case of a cyclopropyl group. No C-H activation takes place alpha to a tertiary center. A detailed DFT study is included and analyses of methyl versus methylene versus methine C-H activation is used to rationalize experimentally observed regio- and enantioselectivities.

Synthesis of imidacloprid derivatives with a chiral alkylated imidazolidine ring and evaluation of their insecticidal activity and affinity to the nicotinic acetylcholine receptor

A series of imidacloprid (IMI) derivatives with an alkylated imidazolidine ring were asymmetrically synthesized to evaluate their insecticidal activity against adult female housefly, Musca domestica, and affinity to the nicotinic acetylcholine receptor of the flies. The bulkier the alkyl group, the lower was the receptor affinity, but the derivatives methylated and ethylated at the R-5-position of the imidazolidine ring were equipotent to the unsubstituted compound. Quantitative structure-activity relationship (QSAR) analysis of the receptor affinity demonstrated that the introduction of a substituent into the imidazolidine ring was fundamentally disadvantageous, but the introduction of a substituent at the R-5-position was permissible in the case of its small size. The binding model of the synthesized derivatives with the receptor supported the QSAR analysis, indicating the existence of space for a short alkyl group around the R-5-position in the ligand-binding site. In addition, positive correlation was observed between the insecticidal activity and receptor affinity, suggesting that the receptor affinity was the primary factor in influencing the insecticidal activity even if the imidazolidine ring was modified.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Efficient synthesis of functionalized aziridinium salts

(Chemical Equation Presented) Various aziridinium salts were efficiently prepared from bromination of a series of backbone substituted N,N-bisubstituted β-amino alcohols and isolated via flash column chromatography. The effect of C-substitution, N-substitution, solvent, leaving group, and counter-anions on formation of the isolable aziridinium salts was investigated. 2009 American Chemical Society.

Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer

Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane ((-)-BPAP), which is a highly potent and selective catecholaminergic activity enhancer (CAE) substance, are described. The synthetic approach consists of the coupling reaction of benzofuran with (R)-N-tosyl-2-propylazirizine or (R)-N-methoxy-N-methylnorvaliamide, followed by appropriate modifications of the resulting coupling products. As the results, (-)-BPAP turned out to have the R configuration, which was finally confirmed by X-ray crystallographic analysis.

Synthesis of macrocyclic insect-derived alkaloids

Macrocyclic lactonic alkaloids found in the pupal secretions of two species of a coccinellid beetle (genus Epilachna) were prepared in enantiomerically pure form via an efficient synthetic route using enantiomerically pure α-amino acids as chiral-pool starting materials. Macrocycles with rings containing up to 98 atoms were synthesized in good yield using Mukaiyama's macrolactonization conditions.

A highly efficient synthesis of (S)-(+)-N-Boc-coniine using ring- closing olefin metathesis (RCM)

Optically active (S)-(+)-coniine as an N-Boc protected form was concisely prepared starting from an amino acid, L-norvaline. The key step involved a ring-closing olefin metathesis (RCM) of the dialkenyl compound 6 to give the corresponding cyclic olefin 8 in an essentially quantitative yield.

Lipase-catalysed Enantioselective Acylation of N-Protected or Unprotected 2-Aminoalkan-1-ols

Porcine pancreatic lipase (PPL) catalysed the acylation of 2-aminoalkan-1-ols; the enantiospecificity depends on the starting amino alcohol.The catalytic activity of the enzyme was markedly improved when the benzyl carbamate derivatives were used as substrates; in general, the enzyme displayed a high enantiospecificity.