145549-11-7

Basic information

• Product Name: (R)-1-BOC-3-PHENYL-PYRROLIDINE
• Synonyms: (R)-1-BOC-3-PHENYL-PYRROLIDINE ;(R)-3-Phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester;tert-butyl(R)-3-phenylpyrrolidine-1-carboxylate
• CAS NO: 145549-11-7
• Molecular Formula: C₁₅H₂₁NO₂
• Molecular Weight: 247.33274
• Mol File: 145549-11-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 342.78 °C at 760 mmHg
• Flash Point: 161.108 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: 2-8°C
• PKA: -1.79±0.40(Predicted)
• CAS DataBase Reference: (R)-1-BOC-3-PHENYL-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-BOC-3-PHENYL-PYRROLIDINE(145549-11-7)
• EPA Substance Registry System: (R)-1-BOC-3-PHENYL-PYRROLIDINE(145549-11-7)

Safety Data

• Hazardous Substances Data: 145549-11-7(Hazardous Substances Data)

Usage

General Description

(R)-1-BOC-3-PHENYL-PYRROLIDINE, also known as (R)-tert-butyl 3-phenylpyrrolidine-1-carboxylate, is a chemical compound with a molecular formula of C16H23NO2. It is a heterocyclic compound with a pyrrolidine ring and a phenyl group, and it is a chiral compound with one stereo center. This chemical is commonly used as a building block in the synthesis of various pharmaceuticals and biologically active compounds. It is also used as a chiral auxiliary in asymmetric synthesis reactions to control the stereochemistry of the final products. Additionally, (R)-1-BOC-3-PHENYL-PYRROLIDINE has been studied for its potential applications in catalysis and as a ligand in metal-catalyzed reactions.

InChI:InChI=1/C15H21NO2/c1-15(2,3)18-14(17)16-10-9-13(11-16)12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3/t13-/m0/s1

Upstream product

• 2842-37-7 2-(phenethylamino)ethanol 
• 122-78-1 phenylacetaldehyde 
• 182921-00-2 (2-oxoethyl)phenethylcarbamic acid t-butyl ester 
• 949902-88-9 (2-hydroxyethyl)phenethylcarbamic acid t-butyl ester 
• 145549-03-7 (3S,7R,7aR)-3,7-Diphenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 591-51-5 phenyllithium 
• 951742-87-3 (3R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-3-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 145549-09-3 (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol 
• 145549-01-5 (3S,6S,7R,7aR)-5-Oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester 

Downstream Products

• 61586-46-7 (-)-(R)-3-Phenylpyrrolidine 

Relevant articles and documents

Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C-H Alkylation

Radical cyclization represents a powerful strategy for construction of ring structures. Traditional radical cyclization, which is based on radical addition as the key step, necessitates the use of unsaturated substrates. Guided by the concept of metalloradical catalysis, a different mode of radical cyclization that can employ saturated C-H substrates is demonstrated through the development of a Co(II)-based system for catalytic activation of aliphatic diazo compounds for enantioselective radical alkylation of various C(sp3)-H bonds. It allows for efficient construction of chiral pyrrolidines and other valuable 5-membered cyclic compounds. This alternative strategy of radical cyclization provides a new retrosynthetic paradigm to prepare five-membered cyclic molecules from readily available open-chain aldehydes through the union of C-H and C=O elements for C-C bond formation.

The Synthesis of Aracemic 4-Substituted Pyrrolidinones and 3-Substituted Pyrrolidines. An Asymmetric Synthesis of (-)-Rolipram

Conjugate additions of RCuCNLi to the chiral α,β-unsaturated lactam 4 gives almost exclusive exo addition - a reversal in stereochemistry when cuprates were added to chiral lactam 1.The lactams 5 were transformed into 4-substituted pyrrolidinones 8 via a three-step sequence which involved decarbalkoxylation, silane reduction and metal-ammonia benzylamine cleavage.The chemical yields as well as the enantiomeric purity were very high for this process.As an example of the usefulness of this scheme, the antidepressant (-)-Rolipram was prepared in good overall yield.Furthermore, the bicyclic lactams 6 were readily transformed, using alane as the reducing agent, to 3-substituted pyrrolidines 11.Absolute configurations of 8 and 11 were confirmed by comparison with literature assignments which also gave strong support to the facial addition of the cuprates to 4.