(2S)-Pyrrolidin-2-ylmethylamine

Base Information

• Chemical Name: (2S)-Pyrrolidin-2-ylmethylamine
• CAS No.: 69500-64-7
• Molecular Formula: C5H12N2
• Molecular Weight: 100.164
• Hs Code.: 29339900
• European Community (EC) Number: 633-270-9
• Nikkaji Number: J1.142.133D
• Wikidata: Q27094181
• Metabolomics Workbench ID: 56567
• Mol file: 69500-64-7.mol

Synonyms:69500-64-7;(S)-pyrrolidin-2-ylmethanamine;(2S)-PYRROLIDIN-2-YLMETHYLAMINE;[(2S)-pyrrolidin-2-yl]methanamine;(S)-(+)-2-(Aminomethyl)pyrrolidine;(S)-2-(Aminomethyl)pyrrolidine;(S)-2-aminomethylpyrrolidine;(S)-pyrrolidin-2-ylmethylamine;MFCD00191745;1-[(2S)-pyrrolidin-2-yl]methanamine;2-Pyrrolidinemethanamine, (2S)-;D07VDJ;SCHEMBL83314;(2S)-2-Pyrrolidinemethanamine;CHEBI:44632;AUKXFNABVHIUAC-YFKPBYRVSA-N;(2S)-Pyrrolidin-2-yl-methylamine;(2S)-Pyrrolidine-2alpha-methanamine;AKOS006238372;DB03253;FD10638;(S)-(+)-2-(Aminomethyl)pyrrolidine, 97%;EN300-1266321;A854903;Q27094181

Chemical Property of (2S)-Pyrrolidin-2-ylmethylamine

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 3.42mmHg at 25°C
• Refractive Index: n20/D 1.482(lit.)
• Boiling Point: 152.9 °C at 760 mmHg
• PKA: 10.68±0.10(Predicted)
• Flash Point: 48.9 °C
• PSA: 38.05000
• Density: 0.914 g/cm³
• LogP: 0.72620
• 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%,99%, ^*data from raw suppliers

(S)-(+)-2-(Aminomethyl)pyrrolidine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(NC1)CN
• Isomeric SMILES: C1C[C@H](NC1)CN
• Uses: (S)-(+)-2-(Aminomethyl)pyrrolidine can be used as an organocatalyst: For the asymmetric transformation of (S)-alanine. In the asymmetric α-fluorination of linear and branched aldehydes using N-fluorobenzenesulfonamide as the fluorinating agent.It can also be used as a reactant to prepare Schiff base metal complexes with pyrrolidine fragment as a ligand in asymmetric synthesis.

Technology Process of (2S)-Pyrrolidin-2-ylmethylamine

There total 24 articles about (2S)-Pyrrolidin-2-ylmethylamine 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: 92.0%

(2S)-pyrrolidine-2-carbonitrile (204387-53-1) → (S)-2-Aminomethylpyrrolidin (69500-64-7)

Guidance literature:

With hydrogen; In ethanol; at 88 ℃; for 1h; under 45004.5 Torr;

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

upstream raw materials:

L-prolinamide

1-[(2S)-N-Benzylpyrrolidin-2-yl]methanamine

(S)-(-)-1-trityl-2-pyrrolidinecarboxamide

N-benzyl-(S)-proline methyl ester

Downstream raw materials:

(3S,7aS)-3-anilino-1,2,5,6,7,7a-hexahydropyrrolo<1,2-c><1,3,2>diazaphosphole 3-oxide

3-anilino-1,2,5,6,7,7a-hexahydropyrrolo<1,2-c><1,3,2>diazaphosphole 3-oxide

(S)-2-<(3-bromo-2,6-dimethoxybenzamido)methyl>pyrrolidine

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

Refernces

• 1、 An, Feng,Maji, Biplab,Min, Elizabeth,Ofial, Armin R.,Mayr, Herbert. "Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts". supporting information. p. 1526 - 1547. Retrieved 2020/02/04.
• 2、 Ansari, Anas,Ramapanicker, Ramesh. "Enantioselective Synthesis of 2-Aminomethyl and 3-Amino Pyrrolidines and Piperidines through 1,2-Diamination of Aldehydes". . p. 8161 - 8169. Retrieved 2018/07/25.