(R)-1-Boc-3-Phenylpyrrolidine

Base Information

• Chemical Name: (R)-1-Boc-3-Phenylpyrrolidine
• CAS No.: 145549-11-7
• Molecular Formula: C15H21NO2
• Molecular Weight: 247.337
• DSSTox Substance ID: DTXSID10439665
• Nikkaji Number: J522.040H
• Wikidata: Q72450324
• Mol file: 145549-11-7.mol

Synonyms:(R)-1-Boc-3-Phenylpyrrolidine;145549-11-7;(R)-1-Boc-3-Phenyl-pyrrolidine;tert-butyl (3R)-3-phenylpyrrolidine-1-carboxylate;3-Phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester;SCHEMBL1751432;DTXSID10439665;REGWJCQNMMXFBM-ZDUSSCGKSA-N;(R)-3-PHENYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;AKOS015841256;AKOS016001323;CS-0337202;Tert-butyl (R)-3-phenylpyrrolidine-1-carboxylate;Q-102173;(3R)-1-(tert-Butoxycarbonyl)-3beta-phenylpyrrolidine

Chemical Property of (R)-1-Boc-3-Phenylpyrrolidine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.528
• Boiling Point: 342.78 °C at 760 mmHg
• PKA: -1.79±0.40(Predicted)
• Flash Point: 161.108 °C
• PSA: 29.54000
• Density: 1.07 g/cm³
• LogP: 3.34890
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 247.157228913
• Heavy Atom Count: 18
• Complexity: 289

Purity/Quality:

99.3% ^*data from raw suppliers

(R)-1-Boc-3-Phenylpyrrolidine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(C1)C2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC[C@@H](C1)C2=CC=CC=C2

Technology Process of (R)-1-Boc-3-Phenylpyrrolidine

There total 11 articles about (R)-1-Boc-3-Phenylpyrrolidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

(3R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-3-carboxylic acid (951742-87-3,221142-28-5,884048-45-7,939757-89-8) → tert-butyl (R)-3-phenylpyrrolidine-1-carboxylate (145549-11-7)

Guidance literature:

(3R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-3-carboxylic acid; With triethylamine; isobutyl chloroformate; In tetrahydrofuran; at -10 ℃; for 0.5h;

With 2-mercaptopyridine N-oxide; In tetrahydrofuran; at -10 - 20 ℃; for 3h; dark;

With 2-methylpropanethiol-1; In tetrahydrofuran; for 20h; Irradiation (Hg lamp);

Reference yield: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol (145549-09-3) → tert-butyl (R)-3-phenylpyrrolidine-1-carboxylate (145549-11-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 16h; under 760 Torr;

DOI:10.1021/jo00053a012

Reference yield:

phenyllithium (591-51-5) → tert-butyl (R)-3-phenylpyrrolidine-1-carboxylate (145549-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) CuCN / 1.) THF, cyclohexane, ether, -78 deg C to 0 deg C, 2.) THF, -78 deg C, 30 min

2: 1.) ammonium formate / 1.) 5percent Pd/C / 1.) MeOH, 1.5 h, 2.) toluene, reflux, 1.5 h

3: 94 percent / AlCl₃, LiAlH₄ / tetrahydrofuran / 1 h / -78 °C

4: 80 percent / H₂ / 10percent Pd/C / ethyl acetate / 16 h / 760 Torr

With lithium aluminium tetrahydride; aluminium trichloride; hydrogen; ammonium formate; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo00053a012

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol

(3R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-3-carboxylic acid

phenyllithium

Downstream raw materials:

(-)-(R)-3-Phenylpyrrolidine

Refernces

• 1、 -. "Process for the preparation of enantiomerically enriched cyclic beta-aryl or heteroaryl carbocyclic acids". Page/Page column 23. . Retrieved 2008/06/13.