(R)-pyrrolidin-2-ylmethanamine

Base Information

• Chemical Name: (R)-pyrrolidin-2-ylmethanamine
• CAS No.: 72300-69-7
• Molecular Formula: C₅H₁₂N₂
• Molecular Weight: 100.164
• Hs Code.: 2933998090
• European Community (EC) Number: 615-751-5
• DSSTox Substance ID: DTXSID00388779
• Nikkaji Number: J385.715H
• Wikidata: Q27122084
• Metabolomics Workbench ID: 57435
• Mol file: 72300-69-7.mol

Synonyms:(R)-pyrrolidin-2-ylmethanamine;72300-69-7;[(2R)-pyrrolidin-2-yl]methanamine;(R)-pyrrolidin-2-ylmethylamine;1-[(2R)-pyrrolidin-2-yl]methanamine;(R)-2-(AMINOMETHYL)PYRROLIDINE;(R)-C-PYRROLIDIN-2-YL-METHYLAMINE;SCHEMBL82149;CHEBI:50470;DTXSID00388779;AUKXFNABVHIUAC-RXMQYKEDSA-N;[(2R)-2-pyrrolidinylmethyl]amine;(-)-(r)-2-aminomethylpyrrolidine;MFCD03424237;AKOS016842869;[2R,(?)]-Pyrrolidine-2beta-(methanamine);EN300-149181;A854900;Q27122084

Chemical Property of (R)-pyrrolidin-2-ylmethanamine

Chemical Property:

• Vapor Pressure: 3.42mmHg at 25°C
• Boiling Point: 79-85℃ (20 Torr)
• Flash Point: 48.9°C
• PSA: 38.05000
• Density: 0.914g/cm³
• LogP: 0.72620
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Dichloromethane; Methanol
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 100.100048391
• Heavy Atom Count: 7
• Complexity: 54

Purity/Quality:

98%min ^*data from raw suppliers

(R)-Pyrrolidin-2-ylmethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1)CN
• Isomeric SMILES: C1C[C@@H](NC1)CN
• Uses: (R)-Pyrrolidin-2-ylmethanamine is an intermediate in synthesizing Miboplatin (M342100), a platinum coordination complexes which have been identified and developed as new antitumor agents in Japan.

Technology Process of (R)-pyrrolidin-2-ylmethanamine

There total 7 articles about (R)-pyrrolidin-2-ylmethanamine 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: 100.0%

tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate (259537-92-3) → (-)-(R)-2-aminomethylpyrrolidine (57734-57-3,69500-64-7,123654-27-3,72300-69-7)

Guidance literature:

tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate; With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃;

In methanol; dichloromethane; for 1h;

Reference yield: 86.0%

tert-butyl (R)-2-((benzyl(tert-butoxycarbonyl)amino)methyl)pyrrolidine-1-carboxylate → (-)-(R)-2-aminomethylpyrrolidine (57734-57-3,69500-64-7,123654-27-3,72300-69-7)

Guidance literature:

tert-butyl (R)-2-((benzyl(tert-butoxycarbonyl)amino)methyl)pyrrolidine-1-carboxylate; With hydrogenchloride; In ethyl acetate; at 0 ℃; for 1h;

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 14h;

DOI:10.1021/acs.joc.8b00933

Reference yield: 46.1%

(R)-prolinamide (62937-45-5) → (-)-(R)-2-aminomethylpyrrolidine (57734-57-3,69500-64-7,123654-27-3,72300-69-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 33h; Heating;

DOI:10.1002/jps.2600800907

upstream raw materials:

(R)-prolinamide

Z-D-proline

D-Prolin

(2R)-2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

Downstream raw materials:

N-[((2R)-1-{[3,4-bis(methyloxy)phenyl]sulfonyl}-2-pyrrolidinyl)methyl]-3,4-bis(methyloxy)benzenesulfonamide

(4aS,13aR)-8-bromo-10-[(phenylmethyl)oxy]-2,3,4a,5,13,13a-hexahydro-1H-pyrido[1,2-a]pyrrolo[1′,2′:3,4]imidazo[1,2-d]pyrazine-9,11-dione

N-[((2R)-1-{[3,4-bis(methyloxy)phenyl]sulfonyl}-2-pyrrolidinyl)methyl]-3,4-bis(methyloxy)benzenesulfonamide

Refernces

• 1、 Zhu, Qingying,Shen, Haimin,Yang, Zhujin,Ji, Hongbing. "Biomimetic asymmetric Michael addition reactions in water catalyzed by amino-containing β-cyclodextrin derivatives". . p. 1227 - 1234. Retrieved 2016/09/07.
• 2、 Diakos, Connie I.,Zhang, Mei,Beale, Philip J.,Fenton, Ronald R.,Hambley, Trevor W.. "Synthesis, characterisation and in vitro cytotoxicity studies of a series of chiral platinum(II) complexes based on the 2-aminomethylpyrrolidine ligand: X-ray crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N-dimethyl-2(R)-aminomethylpyrrolidine)". experimental part. p. 2807 - 2814. Retrieved 2009/10/10.