1-N-Boc-3-Cyanopyrrolidine

Base Information

• Chemical Name: 1-N-Boc-3-Cyanopyrrolidine
• CAS No.: 476493-40-0
• Molecular Formula: C10H16N2O2
• Molecular Weight: 196.249
• Hs Code.: 2933990090
• European Community (EC) Number: 672-487-3
• DSSTox Substance ID: DTXSID30373537
• Nikkaji Number: J3.141.659K
• Mol file: 476493-40-0.mol

Synonyms:1-N-Boc-3-Cyanopyrrolidine;476493-40-0;tert-butyl 3-cyanopyrrolidine-1-carboxylate;n-boc-3-cyanopyrrolidine;1-boc-3-cyanopyrrolidine;1-boc-3-cyano-pyrrolidine;MFCD03001709;3-Cyano-pyrrolidine-1-carboxylic acid tert-butyl ester;1-PYRROLIDINECARBOXYLIC ACID, 3-CYANO-, 1,1-DIMETHYLETHYL ESTER;1-N-Boc-3-Cyano-pyrrolidine;(r)-1-n-boc-3-cyanopyrrolidine;SCHEMBL56905;DTXSID30373537;VDDMCMFPUSCJNA-UHFFFAOYSA-N;BCP15390;CS-D0751;BBL100743;STL554537;(S)-1-Boc-3-pyrrolidinecarbonitrile;AKOS005255580;AC-9198;DS-0590;PB12838;PB23316;PB27598;SY006279;SY029001;(r,s)-1-n-boc-pyrrolidine-3-carbonitrile;1-(t-butyloxycarbonyl)-3-cyanopyrrolidine;A7290;AM20100190;FT-0600984;FT-0601704;FT-0644720;EN300-68721;B66770;Q-102877;3-cyanopyrrolidine-1-carboxylic acid tert-butyl ester;4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester;Z1095382132;1,1-DIMETHYLETHYL 3-CYANO-1-PYRROLIDINECARBOXYLATE

Chemical Property of 1-N-Boc-3-Cyanopyrrolidine

Chemical Property:

• Vapor Pressure: 0.000703mmHg at 25°C
• Melting Point: -108 °C
• Refractive Index: 1.488
• Boiling Point: 307.9 °C at 760 mmHg
• PKA: -3.73±0.40(Predicted)
• Flash Point: 140 °C
• PSA: 53.33000
• Density: 1.08 g/cm³
• LogP: 1.70488
• Storage Temp.: 2-8°C
• XLogP3: 1
• 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

1-N-Boc-3-cyanopyrrolidine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(C1)C#N
• Uses: 1-N-Boc-3-cyanopyrrolidine is used to prepare aroyl-substituted pyrrolidines with monoamine reuptake inhibition activities.

Technology Process of 1-N-Boc-3-Cyanopyrrolidine

There total 9 articles about 1-N-Boc-3-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: 98.0%

sodium cyanide (773837-37-9) + 3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (141699-57-2) → 3-cyanopyrrolidine-1-carboxylic acid tert-butyl ester (476493-40-0)

Guidance literature:

In N,N-dimethyl-formamide; at 100 ℃; for 16h;

Reference yield: 70.0%

lithium cyanide (788104-34-7,25733-05-5) + 3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (141699-57-2) → 3-cyanopyrrolidine-1-carboxylic acid tert-butyl ester (476493-40-0)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 16h;

Reference yield: 62.0%

P-toluenesulfonyl cyanide (19158-51-1) + potassium (1-(tert-butoxycarbonyl)pyrrolidin-3-yl)trifluoroborate → 3-cyanopyrrolidine-1-carboxylic acid tert-butyl ester (476493-40-0)

Guidance literature:

With 9-(2-mesityl)-10-methylacridinium perchlorate; In N,N-dimethyl-formamide; at 30 - 35 ℃; for 18h; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.6b01207

upstream raw materials:

1-tert-<(butyloxy)carbonyl>-3-carbamoylpyrrolidine

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine

lithium cyanide

3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

1-tert-<(butyloxy)carbonyl>-3-(thiocarbamoyl)pyrrolidine

1-(4-(methylsulfonyl)phenyl)pyrrolidine-3-carbonitrile

racemic pyrrolidine-3-carbonitrile

tert-butyl 3-[(Z)-amino(hydroxyimino)methyl]pyrrolidine-1-carboxylate

Refernces

• 1、 Shi, Qing,Meehan, Mariah C.,Galella, Michael,Park, Hyunsoo,Khandelwal, Purnima,Hynes, John,Dhar, T. G. Murali,Marcoux, David. "Protected Chloroethyl and Chloropropyl Amines as Conformationally Unrestricted Annulating Reagents". supporting information. p. 337 - 340. Retrieved 2018/01/28.
• 2、 -. "Glutaminase inhibitors as well as compositions and applications thereof". . . Retrieved 2018/01/09.