14468-80-5

Basic information

• Product Name: N-CBZ-2-Pyrrolidinone
• Synonyms: N-CBZ-2-Pyrrolidinone;1-Z-2-Pyrrolidinone;1-(Benzyloxycarbonyl)-2-pyrrolidinone;N-Benzyloxycarbonylpyrrolidin-2-one;1-Z-2-Pyrrolidinone 97%;benzyl 2-oxopyrrolidine-1-carboxylate;1-Cbz-2-oxo-pyrrolidine;1-Pyrrolidinecarboxylic acid, 2-oxo-, phenylmethyl ester
• CAS NO: 14468-80-5
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.23652
• Mol File: 14468-80-5.mol

Chemical Properties

• Melting Point: 32-36°C
• Boiling Point: 147 °C(Press: 0.1 Torr)
• Flash Point: >110℃
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• PKA: -2.26±0.20(Predicted)
• CAS DataBase Reference: N-CBZ-2-Pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: N-CBZ-2-Pyrrolidinone(14468-80-5)
• EPA Substance Registry System: N-CBZ-2-Pyrrolidinone(14468-80-5)

Safety Data

• Statements: 52/53
• Safety Statements: 61
• WGK Germany: 3
• Hazardous Substances Data: 14468-80-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-CBZ-2-Pyrrolidinone is used as a key intermediate in the synthesis of pharmaceuticals for its ability to facilitate the production of a wide range of medicinal compounds. Its role in drug development is crucial due to its compatibility with various chemical reactions required for creating effective treatments.
Used in Agrochemical Industry:
In the agrochemical sector, N-CBZ-2-Pyrrolidinone serves as an essential intermediate in the synthesis of various agrochemicals, contributing to the development of products that enhance crop protection and yield.
Used as a Solvent:
N-CBZ-2-Pyrrolidinone is utilized as a solvent in numerous industrial applications, capitalizing on its ability to dissolve a broad spectrum of substances, which is vital for processes that require the mixing or dissolution of different compounds.
Used in Organic Compound Synthesis:
N-CBZ-2-Pyrrolidinone is also used as a building block in the synthesis of other organic compounds, highlighting its versatility and importance in organic chemistry for creating new materials and substances with specific properties for various applications.

Upstream product

• 5105-78-2 4-(benzyloxycarbonylamino)butyric acid 
• 86136-88-1 pent-4-enylcarbamic acid benzyl ester 
• 616-45-5 2-pyrrolidinon 
• 865-47-4 potassium tert-butylate 
• 1885-14-9 phenyl chloroformate 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 5532-86-5 benzyl cyanoformate 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 120-51-4 benzoic acid benzyl ester 
• 69352-30-3 benzyl (N-(4-phenyl-4-oxobutyl)amino)methanoate 
• 927390-70-3 (3-dimethylcarbamoylpropyl)carbamic acid benzyl ester 
• 91189-06-9 N-Ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidine-carboxamide 
• 160133-30-2 1-Benzyloxycarbonyl-3-(tert.butyloxycarbonylmethyl)-2-pyrrolidinone 
• 91189-04-7 N-methyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide 
• 880461-84-7 2-(1-methoxycarbonyl-2-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 174875-59-3 2-(2-oxo-2-phenyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 174875-26-4 2-(2-oxo-pentyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 153749-83-8 2-(2-oxo-2-phenyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 88001-42-7 benzyl 2-methoxypyrrolidine-1-carboxylate 
• 96096-65-0 N-[2-(5-methoxy-1H-indol-3-yl)ethyl]benzyloxycarboxamide 
• 68471-57-8 2,3-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 360566-07-0 2-((E)-4-Oxo-oct-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Construction of a (3 aR,4 R,9 bR)-Hexahydropyrroloquinoline by Stereoselective Hydrogen-Mediated Domino Cyclization

A novel practical asymmetric route to a chiral hexahydropyrroloquinoline derivative 2, a key fragment of TAK-480, is reported. The corresponding substrate, enamine 19, was directly transformed to a diastereopure and enantiopure (3aR,4R,9bR)-hexahydropyrroloquinoline 16 through a rhodium-catalyzed hydrogen-mediated domino cyclization consisting of four steps; (1) asymmetric hydrogenation of enamine, (2) hydrogenation of iminium olefin in a lactam, (3) dehydration and catalytic sulfonation, and (4) cis-selective intramolecular cyclization. A tuned asymmetric catalyst [Rh(cod){(2S,4S)-PTBP-SKEWPHOS}]OTf that we previously developed was found to promote improved reaction activity and be the most suitable catalyst for a multikilogram manufacturing for preclinical research. The resulting stereoselective domino cyclization drastically reduced several synthetic steps, and the resulting waste compared to the discovery route that required chiral preparative high-performance liquid chromatography and silica gel column separation.

Enantioselective synthesis of 3-hydroxypiperidin-2-ones

An efficient synthesis of (S)- and (R)-3-hydroxypiperidin-2-ones from methyl 5-nitro-2-oxopentanoate is described. A one-pot enzyme catalysed hydrolysis of the ester and reduction of the ketone gave enantiopure 2- hydroxy-5-nitropentanoic acids which on esterification, catalytic hydrogenation over a platinum(IV) oxide catalyst and intramolecular: cyclisation gave the target compounds in 93% overall yield and >99% ee.

One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles

A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.

2 - Trifluoromethyl - 1 - benzyloxycarbonyl - 1 - nitrogen heterocyclic alkane preparation method

The invention discloses a preparation method of 2-trifluoromethyl-1-carbobenzoxy-1-aza-cyclane, and mainly solves the problems that the step of the preparation of alpha-position trifluoromethyl aza-cyclane is long, the yield is low, and the like. The meth

RHODIUM CATALYST AND METHOD FOR PRODUCING AMINE COMPOUND

[Problem] Provision of a superior rhodium catalyst and a production method of amine compound. [Solving Means] A rhodium complex coordinated with a compound represented by the formula

Enzymatic and chromatographic resolution procedures applied to the synthesis of the phosphoproline enantiomers

The preparation of enantiomerically pure pyrrolidine-2-phosphonic acid (phosphoproline, ProP) has been addressed through the synthesis of suitable racemates and subsequent resolution by independent enzyme-catalyzed and chiral HPLC methods. First, racemic phosphoproline derivatives bearing the necessary protecting groups have been synthesized in excellent global yields starting from inexpensive materials. Preparative HPLC resolution of the N-Cbz-protected aminophosphonate on a cellulose-based column allowed the isolation of enantiomerically pure enantiomers on a gram scale. Enzyme-catalyzed alkoxycarbonylation of the aminophosphonate was studied using different lipases, solvents, and carbonates. Candida antarctica lipase type A (CAL-A) provided the highest enantioselectivity when combined with benzyl 3-methoxyphenyl carbonate.

Hydrozirconation of four-, five-, six- and seven-membered N-alkoxycarbonyl lactams to lactamols

A general, practical, and efficient reduction of four-, five-, six- and, seven-membered N-alkoxycarbonyl lactams to the aldehyde oxidation state is reported. The reduction methodology involves the hydrozirconation reaction by Cp2Zr(H)Cl under m

A facile approach to trans-4,5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine

An efficient approach to trans-4-hydroxylpyrrolidine lactams 1 starting from amino acid is described. The utility of this method has been demonstrated in the synthesis of antipsychotic nemonapride 3 and antiangiogenic streptopyrrolidine 4. Compared four s

Catalytic, asymmetric vinylogous Mukaiyama aldol reactions of pyrrole- and furan-based dienoxy silanes: How the diene heteroatom impacts stereocontrol

Denmark's chiral bisphosphoramide/silicon tetrachloride system performs as an excellent Lewis base-Lewis acid catalyst for the vinylogous Mukaiyama aldol reaction of pyrrole- and furan-based dienoxy silanes with aromatic and heteroaromatic aldehydes. This asymmetric methodology provides a powerful synthetic entry to a variety of d-hydroxylated g-butenolide-type frameworks with high efficiency and valuable margins of regio-, diastereo-, and enantioselectivity. Notably, the nature of the heteroatom within the vinylogous dienoxy silane donor heavily impacts the diastereocontrol, with syn-configured aldol adducts emerging from pyrroles bearing electron- withdrawing N-protecting groups (Boc, Ts, and Cbz) and anti-configured adducts prevailing when furan- or N-alkyl/alkenylpyrrole donors are involved.

De novo asymmetric approach to 8a-epi-Swainsonine

An improved method for the synthesis of (-)-8a-epi-swainsonine has been developed with 9 fewer steps than the original route. The synthetic improvements include a two-step procedure for the preparation of benzyl 4-(furan-2-yl)-4-oxobutylcarbamate from pyr