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
• Article Data: 4

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

N-Boc-2-pyrrolidinone is a useful synthetic intermediate. It can be used to prepare highly functionalized N-acyl-2-vinylpyrrolidines by a 4-component Ugi reaction (isocyanide, carbonyl compounds, primary amines, carboxylic acids). It can also be used to synthesize the naturally occurring Maillard flavors via catalytic SeO2 oxidation.

General Description

The kinetics of gas-phase elimination of 1-(tert-butoxycarbonyl)-2-pyrrolidinone has been investigated in a static system. The observed rate coefficient has been reported to be log k1(s-1) = (11.54 ± 0.29) -(140.8 ± 2.8)-kJmol-1 (2.303RT)-1.

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

• 116437-41-3 tert-butyl (4-oxo-4-phenyl-butyl)-carbamate 
• 913573-39-4 methyl 4-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoyl]benzoate 
• 914954-34-0 tert-butyl (4-(3-methoxyphenyl)-4-oxobutyl)carbamate 
• 1015069-81-4 tert-butyl 3-benzyl-2-oxopyrrolidine-1-carboxylate 
• 1172067-26-3 4-(tert-butoxycarbonylamino)-2-(4-chlorobenzyl)butanoic acid 
• 914954-39-5 tert-butyl [4-(2-methoxyphenyl)-4-oxobutyl]carbamate 
• 1309359-79-2 tert-butyl 5-oxoazocane-1-carboxylate 
• 1223405-24-0 tert-butyl (4-(3-fluorophenyl)-4-oxobutyl)carbamate 

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.

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.