tert-Butyl 2-cyanopiperidine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 2-cyanopiperidine-1-carboxylate
• CAS No.: 153749-89-4
• Molecular Formula: C11H18N2O2
• Molecular Weight: 210.27
• Hs Code.: 2933399090
• European Community (EC) Number: 672-484-7
• DSSTox Substance ID: DTXSID50373534
• Nikkaji Number: J2.540.440H
• Mol file: 153749-89-4.mol

Synonyms:153749-89-4;tert-Butyl 2-cyanopiperidine-1-carboxylate;1-Boc-2-cyanopiperidine;N-Boc-2-Cyanopiperidine;1-N-Boc-2-Cyanopiperidine;(+/-)-1-n-boc-2-cyano-piperidine;MFCD01861221;2-cyano-piperidine-1-carboxylic acid tert-butyl ester;N-Boc-2-piperidinecarbonitrile;1-Piperidinecarboxylic acid, 2-cyano-, 1,1-dimethylethyl ester;1-boc-2-Cyano-piperidine;1-Boc-piperidine-2-carbonitrile;1-n-boc-2-cyano-piperidine;SCHEMBL3966030;1-piperidinecarboxylic acid, 2-cyano-, 1,1-dimethylethyl ester, (2s)-;DTXSID50373534;LKAJZBMOVZIKHA-UHFFFAOYSA-N;CS-D0646;RAC 1-BOC-2-CYANOPIPERIDINE;AKOS005146147;AB19944;DS-1465;MB02080;SB22028;1-Boc-piperidine-2-carbonitrile, 95%;SY025697;TS-02991;A3382;AM20080391;FT-0601673;FT-0655756;FT-0773897;EN300-56142;B66753;1-(tert-Butoxycarbonyl)piperidine-2-carbonitrile;DIMETHYL 3-(AMINOMETHYL)BENZYLPHOSPHONATE;W-205749;Z851015570

Chemical Property of tert-Butyl 2-cyanopiperidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.000232mmHg at 25°C
• Melting Point: 62-67℃
• Refractive Index: 1.487
• Boiling Point: 325.3 °C at 760 mmHg
• PKA: -4.85±0.40(Predicted)
• Flash Point: 150.5 °C
• PSA: 53.33000
• Density: 1.07 g/cm³
• LogP: 2.23748
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 210.136827821
• Heavy Atom Count: 15
• Complexity: 285

Purity/Quality:

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

tert-Butyl2-Cyanopiperidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCCC1C#N

Technology Process of tert-Butyl 2-cyanopiperidine-1-carboxylate

There total 15 articles about tert-Butyl 2-cyanopiperidine-1-carboxylate 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: 97.0%

rac-N-(tert-butoxycarbonyl)piperidine-2-carboxamide (388077-74-5) → 2-cyanopiperidine-1-carboxylic acid tert-butyl ester (153749-89-4)

Guidance literature:

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; acetonitrile; at -5 - 20 ℃;

Reference yield: 96.0%

trimethylsilyl cyanide (7677-24-9) + t-butyl piperidinecarboxylate (75844-69-8) → 2-cyanopiperidine-1-carboxylic acid tert-butyl ester (153749-89-4)

Guidance literature:

With methanesulfonic acid; N,N,N,N-tetraethylammonium tetrafluoroborate; In dichloromethane; acetonitrile; at 0 ℃; Electrochemical reaction;

DOI:10.1039/b816598j

Reference yield: 91.0%

CN(1-)*C3H9NPol(1+) + t-butyl piperidinecarboxylate (75844-69-8) → 2-cyanopiperidine-1-carboxylic acid tert-butyl ester (153749-89-4)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In acetonitrile; at 20 ℃; Electrochemical reaction;

DOI:10.1021/ja804048a

upstream raw materials:

trimethylsilyl cyanide

1-t-butoxycarbonyl-2-tributylstannylpiperidine

N-tert-butoxycarbonyl-2-ethoxypiperidine

piperidine-2-carbonitrile

Downstream raw materials:

tert-butyl 2-(2-chloroethyl)-2-cyanopiperidine-1-carboxylate

3-(3-piperidin-2-yl-[1,2,4]oxadiazol-5-yl)-benzonitrile

Refernces

• 1、 -. "PROCESS FOR THE PRODUCTION OF COBIMETINIB". Page/Page column 29. . Retrieved 2019/05/22.
• 2、 Wakaki, Takayuki,Sakai, Kentaro,Enomoto, Takafumi,Kondo, Mio,Masaoka, Shigeyuki,Oisaki, Kounosuke,Kanai, Motomu. "C(sp3)?H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis". supporting information. p. 8051 - 8055. Retrieved 2018/06/15.