(S)-1-Boc-2-cyanopyrrolidine

Base Information

• Chemical Name: (S)-1-Boc-2-cyanopyrrolidine
• CAS No.: 228244-04-0
• Molecular Formula: C10H16N2O2
• Molecular Weight: 196.249
• Hs Code.: 29339900
• European Community (EC) Number: 672-481-0
• DSSTox Substance ID: DTXSID10426237
• Nikkaji Number: J2.445.459B
• Wikidata: Q72448999
• ChEMBL ID: CHEMBL1081012
• Mol file: 228244-04-0.mol

Synonyms:228244-04-0;(S)-1-Boc-2-cyanopyrrolidine;tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate;(S)-tert-butyl 2-cyanopyrrolidine-1-carboxylate;(s)-1-n-boc-2-cyanopyrrolidine;(S)-1-N-BOC-2-CYANO-PYRROLIDINE;(S)-1-Boc-2-pyrrolidinecarbonitrile;(S)-(-)-1-BOC-2-CYANOPYRROLIDINE;MFCD01861224;1-PYRROLIDINECARBOXYLIC ACID, 2-CYANO-, 1,1-DIMETHYLETHYL ESTER, (2S)-;(S)-1-(tert-Butoxycarbonyl)-2-cyanopyrrolidine;(S)-(-)-1-Boc-2-pyrrolidinecarbonitrile;(S)-1-Boc-2-cyano-pyrrolidine;BOC-2(S)-cyanopyrrolidine;(S)-1-(tert-Butoxycarbonyl)-2-pyrrolidinecarbonitrile;SCHEMBL1357066;1-N-Boc-2- pyrrolidinonitrile;CHEMBL1081012;(R)-N-BOC-2-pyrrolidinonitrile;DTXSID10426237;MDMSZBHMBCNYNO-QMMMGPOBSA-N;Boc-(S)-pyrrolidine-2-carbonitrile;AKOS005258731;AKOS015898281;(S)-1-Boc-pyrrolidine-2-carbonitrile;AC-2243;DS-1434;PD139958;A4857;AM20090231;B4878;CS-0001898;(S)-tert-butyl2-cyanopyrrolidine-1-carboxylate;B66764;EN300-248514;tert-Butyl (S)-2-Cyano-1-pyrrolidinecarboxylate;tert-butyl(2S)-2-cyano-1-pyrrolidinecarboxylate;(S)-(-)-1-Boc-2-pyrrolidinecarbonitrile, 97%;Q-102169;TERT-BUTYL (2S)-2-CYANO-1-PYRROLIDINECARBOXYLATE;Z1255373042;(2S)-2-Cyanopyrrolidine-1-carboxylic acid tert-butyl ester;(S)-2-Cyano-1-pyrrolidinecarboxyic Acid tert-Butyl Ester;(s)-2-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (S)-1-Boc-2-cyanopyrrolidine

Chemical Property:

• Melting Point: 33-36 °C
• Boiling Point: 307.9 °C at 760 mmHg
• PKA: -4.97±0.40(Predicted)
• Flash Point: 140 °C
• PSA: 53.33000
• Density: 1.08 g/cm³
• LogP: 1.84738
• Storage Temp.: Room temperature.
• Sensitive.: Moisture & Light Sensitive
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 196.121177757
• Heavy Atom Count: 14
• Complexity: 272

Purity/Quality:

99% ^*data from raw suppliers

(S)-(-)-1-Boc-2-cyanopyrrolidine ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C#N
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1C#N
• Uses: (S)-(-)-1-Boc-2-pyrrolidinecarbonitrile is used in synthesis of prolyl oligopeptidase inhibitors and is a reagent that is used in the design of potent and selective inhibitors of DPP-4 that exhibits an attractive pharmacokinetic profile as antidiabetics. Used in synthesis of prolyl oligopeptidase inhibitors.

Technology Process of (S)-1-Boc-2-cyanopyrrolidine

There total 2 articles about (S)-1-Boc-2-cyanopyrrolidine 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:

acetonitrile (75-05-8,26809-02-9) + (S)-2-(hydroxyiminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester → (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate (35150-07-3) + tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate (228244-04-0)

Guidance literature:

With copper diacetate; In ethyl acetate; at 70 ℃; for 4h;

DOI:10.1055/a-1549-0903

Reference yield:

(S)-2-(hydroxyiminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester → (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate (35150-07-3) + tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate (228244-04-0)

Guidance literature:

With copper diacetate; acetonitrile; In ethyl acetate; at 70 ℃; for 4h; Temperature; Time; Reagent/catalyst; Catalytic behavior;

DOI:10.1002/open.202100230

Reference yield: 85.0%

benzoic acid hydrazide (613-94-5) + tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate (228244-04-0) → (S)-2-(5-phenyl-4H-[1,2,4]triazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1252038-20-2)

Guidance literature:

With potassium carbonate; In butan-1-ol; at 125 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/cmdc.201900618

upstream raw materials:

acetonitrile

Downstream raw materials:

(2S)-pyrrolidine-2-carbonitrile 4-methylbenzene-1-sulfonic acid

(S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-1-(4-(9-cyclohexylnonyl)benzoyl)pyrrolidine-2-carbonitrile

VPC₁₄₃v47