2-Bromomethyl-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 2-Bromomethyl-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 86954-06-5
• Molecular Formula: C13H16BrNO2
• Molecular Weight: 298.17564
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30518800
• Mol file: 86954-06-5.mol

Synonyms:2-Bromomethyl-pyrrolidine-1-carboxylic acid benzyl ester;86954-06-5;benzyl 2-(bromomethyl)pyrrolidine-1-carboxylate;SCHEMBL7312769;DTXSID30518800;SB48469;AM101416;CS-0456556;EN300-12581942;2-Bromomethyl-pyrrolidine-1-carboxylicacidbenzylester

Chemical Property of 2-Bromomethyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

• PSA: 29.54000
• LogP: 3.12040
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 297.03644
• Heavy Atom Count: 17
• Complexity: 254

Purity/Quality:

≥95% ^*data from raw suppliers

2-Bromomethyl-pyrrolidine-1-carboxylicacidbenzylester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)CBr

Technology Process of 2-Bromomethyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 5 articles about 2-Bromomethyl-pyrrolidine-1-carboxylic acid benzyl ester 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: 79.0%

pent-4-enylcarbamic acid benzyl ester (86136-88-1) → N-<(Benzyloxy)carbonyl>-2-(bromomethyl)pyrrolidine (86954-06-5)

Guidance literature:

With N-Bromosuccinimide; 1,1,1,3',3',3'-hexafluoro-propanol; In dichloromethane; at -40 ℃; for 1h; Sealed tube;

DOI:10.1002/anie.202010846

Reference yield: 60.0%

(S)-2-hydroxymethyl-1-pyrrolidine carboxylic acid phenylmethyl ester (86954-05-4) → N-<(Benzyloxy)carbonyl>-2-(bromomethyl)pyrrolidine (86954-06-5)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In acetonitrile; Ambient temperature;

DOI:10.1021/jo00170a037

Reference yield: 48.0%

Z-prolinol (6216-63-3,50463-96-2,72597-18-3,86954-05-4) → 1-Z-2-(bromomethyl)pyrrolidine (86954-06-5,128510-24-7,128510-27-0)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In acetonitrile; for 8h; Ambient temperature;

DOI:10.1271/bbb1961.55.37

upstream raw materials:

(S)-2-hydroxymethyl-1-pyrrolidine carboxylic acid phenylmethyl ester

N-carbobenzyloxyproline

carbon tetrabromide

triphenylphosphine

Downstream raw materials:

N-<(Benzyloxy)carbonyl>-2-(2-acetyl-3-oxobutyl)pyrrolidine

1-<(1-Z-pyrrolidine-2-yl)methyl>pyrrolidine

3-<(1-Z-pyrrolidine-2-yl)methyl>thiazolidine

Refernces

• 1、 Yoshimoto,Tsuru,Yamamoto,Ikezawa,Furukawa. "Structure activity relationship of inhibitors specific for prolyl endopeptidase.". . p. 37 - 43. Retrieved 2007/10/02.
• 2、 Mori, Miwako,Washioka, Yumiko,Urayama, Takao,Yoshiura, Kagari,Chiba, Katsumi,Ban, Yoshio. "Palladium-Catalyzed Carbonylation. A New Synthesis of α-Methylene γ-, δ-, and ε-Lactams and -Lactones Including Bicyclic Lactams of Pyrrolizidine and Indolizidine Skeletons". . p. 4058 - 4067. Retrieved 2007/10/02.