Tert-butyl 2-phenylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 2-phenylpyrrolidine-1-carboxylate
• CAS No.: 154874-88-1
• Molecular Formula: C15H21NO2
• Molecular Weight: 247.337
• DSSTox Substance ID: DTXSID60396214
• Nikkaji Number: J575.915C
• Mol file: 154874-88-1.mol

Synonyms:Tert-butyl 2-phenylpyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylic acid, 2-phenyl-, 1,1-dimethylethyl ester, (2S)-;154874-88-1;SCHEMBL6960066;2-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester;DTXSID60396214;NRRWLVIUZOVWTI-UHFFFAOYSA-N;AKOS013099403;1-(tert-Butoxycarbonyl)-2-phenylpyrrolidine;FT-0774155;tert-butyl 2-phenyl-1-pyrrolidinecarboxylate;2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of Tert-butyl 2-phenylpyrrolidine-1-carboxylate

Chemical Property:

• PSA: 29.54000
• LogP: 3.69650
• XLogP3: 3.1
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C2=CC=CC=C2

Technology Process of Tert-butyl 2-phenylpyrrolidine-1-carboxylate

There total 46 articles about Tert-butyl 2-phenylpyrrolidine-1-carboxylate 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + 1-(4-azidobutyl)benzene (7332-01-6) → (±)-tert-butyl-2-phenylpyrrolidine-1-carboxylate (154874-88-1)

Guidance literature:

With iron(II)-tetra-tert-butylphthalocyaninato complex with an axial pyridine ligand; In toluene; at 130 ℃; Reagent/catalyst; Temperature; Catalytic behavior; Schlenk technique; Inert atmosphere;

DOI:10.1039/d1cc04573c

Reference yield: 82.0%

tert-butyl benzyl(3-chloropropyl)carbamate (154874-86-9) → (±)-tert-butyl-2-phenylpyrrolidine-1-carboxylate (154874-88-1)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; at -78 ℃; for 5h;

DOI:10.1021/jo00081a002

Reference yield: 80.0%

bromobenzene (108-86-1,52753-63-6) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → (±)-tert-butyl-2-phenylpyrrolidine-1-carboxylate (154874-88-1)

Guidance literature:

With nickel(II) bromide dimethoxyethane; dipotassium hydrogenphosphate; benzaldehyde; 4,4'-di-tert-butyl-2,2'-bipyridine; In acetone; at -78 - 20 ℃; for 72h; Reagent/catalyst; Solvent; Catalytic behavior; Inert atmosphere; UV-irradiation;

DOI:10.1021/acs.orglett.9b02226

upstream raw materials:

tert-butyl benzyl(3-chloropropyl)carbamate

iodobenzene

2-(phenyl)pyrrolidine

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl (4-oxo-4-phenyl-butyl)-carbamate

C₁₆H₂₁NO₄

2-phenyl pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(S)-2-phenyl-2-phenylcarbamoylpyrrolidine-1-carboxylic acid tert-butyl ester