85909-08-6

Basic information

• Product Name: 1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE
• Synonyms: N-BOC-1-AZACYCLOPENTAN-2-ONE;1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE;2-OXO-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;AIDS143102;tert-Butyl 2-oxo-1-pyrrolidinecarboxylate;Pyrrolidin-2-one, N-BOC protected;1-(tert-Butoxycarbonyl)-2-oxopyrrolidine, tert-Butyl 2-oxopyrrolidine-1-carboxylate;1-BOC-Pyrrolidin-2-one
• CAS NO: 85909-08-6
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.22
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyrrolidines;Building Blocks;C4 to C10;Chemical Synthesis;Heterocyclic Building Blocks;NSC 662770
• Mol File: 85909-08-6.mol

Chemical Properties

• Boiling Point: 100-105 °C/0.5 mmHg(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 1.086 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000975mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: -2.21±0.20(Predicted)
• CAS DataBase Reference: 1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE(85909-08-6)
• EPA Substance Registry System: 1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE(85909-08-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 85909-08-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE is used as a synthetic intermediate for the preparation of highly functionalized N-acyl-2-vinylpyrrolidines through a 4-component Ugi reaction. This reaction involves isocyanide, carbonyl compounds, primary amines, and carboxylic acids, and is crucial for the development of new pharmaceutical compounds.
Used in Flavor and Fragrance Industry:
1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE is used as a precursor for the synthesis of naturally occurring Maillard flavors. These flavors are essential in the food and beverage industry for enhancing taste and aroma. The synthesis is achieved through catalytic SeO2 oxidation, which allows for the production of a wide range of flavor compounds.

InChI:InChI=1/C9H15NO3/c1-9(2,3)13-8(12)10-6-4-5-7(10)11/h4-6H2,1-3H3

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 

Downstream Products

• 85909-04-2 4-tert-butoxycarbonylaminobutyric acid methyl ester 
• 116437-41-3 tert-butyl (4-oxo-4-phenyl-butyl)-carbamate 
• 106412-40-2 tert-butyl 2-ethoxypyrrolidine-1-carboxylate 
• 616-45-5 2-pyrrolidinon 
• 144403-11-2 (3-Cyclohexylcarbamoyl-propyl)-carbamic acid tert-butyl ester 
• 144403-09-8 N-benzyl-3-(N-Boc)aminobutanamide 
• 193264-88-9 2-oxo-pyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1-tert-butyl ester 
• 344771-92-2 5-(N-carbo-tert-butoxy)amino-1-phenylsulfonyl-2-pentanone 
• 431079-79-7 1-(tert-butyl) 3-methyl 2-oxopyrrolidine-1,3-dicarboxylate 
• 115-11-7 isobutene 
• 320343-60-0 (R)-N-tert-butoxycarbonyl-4-hydroxy-pyrrolidin-2-one 
• 320343-58-6 (S)-N-tert-butoxycarbonyl-4-hydroxy-pyrrolidin-2-one 
• 646062-88-6 (E)-(6-tert-butoxycarbonylamino)-2-hexenal 

Relevant articles and documents

Selective C(sp3)?H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow

A mild and selective C(sp3)?H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C?H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (?)-ambroxide, pregnenolone acetate, (+)-sclareolide, and artemisinin, exemplifies the utility of this new method.

Oxidative transformation of cyclic ethers/amines to lactones/lactams using a DIB/TBHP protocol

A novel C-H oxidation of cyclic ethers and amines to the corresponding lactones and lactams was developed using a DIB/TBHP protocol. The reaction is mild and no metallic reagent is involved. In addition, study shows that the electronic properties of the substituents could affect the selectivity of oxidation. The Royal Society of Chemistry 2013.

Process and intermediates to a tetrahydro-[1,8]- Naphthyridine

A novel process is provided for the preparation of 3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)-propylamine which is useful in the synthesis of αv integrin receptor antagonists. Also provided are useful intermediates obtained from the process.

Radical oxidation of amides and related compounds with hypervalent tert- butylperoxyiodanes: Synthesis of imides and tert-butylperoxyamide acetals

tert-Butylperoxyiodane undergoes oxidation of the methylene groups α to the nitrogen atom of amides (or carbamates) yielding imides or tert- butylperoxyamide acetals, depending on the reaction conditions. A proposed mechanism involves generation of carbon-centered radicals α to the nitrogen atom.