(R)-5-(Pyrrolidin-2-YL)-1H-tetrazole

Base Information

• Chemical Name: (R)-5-(Pyrrolidin-2-YL)-1H-tetrazole
• CAS No.: 702700-79-6
• Molecular Formula: C5H9N5
• Molecular Weight: 139.15800
• European Community (EC) Number: 859-366-2
• DSSTox Substance ID: DTXSID20466427
• Nikkaji Number: J2.099.386C
• Wikidata: Q72505520
• Mol file: 702700-79-6.mol

Synonyms:702700-79-6;(R)-5-(PYRROLIDIN-2-YL)-1H-TETRAZOLE;5-[(2R)-pyrrolidin-2-yl]-2H-1,2,3,4-tetrazole;1H-Tetrazole, 5-(2R)-2-pyrrolidinyl-;5-[(2R)-pyrrolidin-2-yl]-2H-tetrazole;(R)-5-(2-Pyrrolidinyl)-1H-tetrazole;MFCD10000886;SCHEMBL2994601;DTXSID20466427;CDB70079;AKOS006376229;AKOS024255828;AS-38677;CS-0050713;P15404;EN300-2908043;A923498;5-[(2R)-pyrrolidin-2-yl]-1H-1,2,3,4-tetrazole

Chemical Property of (R)-5-(Pyrrolidin-2-YL)-1H-tetrazole

Chemical Property:

• Melting Point: 272-274℃
• PSA: 66.49000
• LogP: -0.04700
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Acetic Acid (Slightly), Water (Sparingly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 139.08579531
• Heavy Atom Count: 10
• Complexity: 117

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-[(2R)-Pyrrolidin-2-yl]-2H-1,2,3,4-tetrazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1)C2=NNN=N2
• Isomeric SMILES: C1C[C@@H](NC1)C2=NNN=N2
• Uses: 5-[(2R)-Pyrrolidin-2-yl]-2H-1,2,3,4-tetrazole is widely used as a catalyst for stereoselective Mannich reaction, aldol reaction, and nitro-Michael reaction.

Technology Process of (R)-5-(Pyrrolidin-2-YL)-1H-tetrazole

There total 5 articles about (R)-5-(Pyrrolidin-2-YL)-1H-tetrazole 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: 84.0%

(2R)-2-(1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester (839711-73-8) → (R)-5-(pyrrolidin-2-yl)-1H-tetrazole (702700-79-6)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In methanol; at 20 ℃; for 4h;

DOI:10.1039/b414742a

Reference yield: 78.0%

5-((R)-1-(9H-fluoren-9-yl)pyrrolidin-2-yl)-1-((R)-1-phenylethyl)-1H-tetrazole → (R)-5-(pyrrolidin-2-yl)-1H-tetrazole (702700-79-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; for 72h; under 2068.65 Torr;

DOI:10.1039/c8gc01544a

Reference yield:

Z-D-proline (6404-31-5) → (R)-5-(pyrrolidin-2-yl)-1H-tetrazole (702700-79-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1-hydroxybenzotriazole; EDCI / tetrahydrofuran / 0.5 h / 20 °C

1.2: 68 percent / aq. NH₃ / tetrahydrofuran / 24 h / 20 °C

2.1: 64 percent / p-TsCl; pyridine / CH₂Cl₂ / 72 h / 20 °C

3.1: 82 percent / NH₄Cl; NaN₃ / dimethylformamide / 8 h / 90 °C

4.1: 84 percent / H₂; aq. acetic acid / Pd/C / methanol / 4 h / 20 °C

With pyridine; sodium azide; hydrogen; ammonium chloride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; p-toluenesulfonyl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b414742a

upstream raw materials:

(2R)-2-(1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Z-D-proline

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

(+)-(R)-2-cyano-pyrrolidine-1-carboxylic acid benzyl ester

Downstream raw materials:

2-(1-methyl-1-phenyl-ethyl)-5-(R)-pyrrolidin-2-yl-2H-tetrazole

(Z,6S,10aR)-5-benzylimino-6-iso-butyl-8,9,10,10a-tetrahydro-6H-tetrazolo[1,5-a]pyrrolo[2,1-c]pyrazine

Refernces

• 1、 Lang, Jan Hendrik,Jones, Peter G.,Lindel, Thomas. "Total Synthesis of the Marine Natural Product Hemiasterlin by Organocatalyzed α-Hydrazination". supporting information. p. 12714 - 12717. Retrieved 2017/09/25.