1-N-Boc-pyrrolidin-2-ylboronic acid

Base Information

• Chemical Name: 1-N-Boc-pyrrolidin-2-ylboronic acid
• CAS No.: 149682-75-7
• Molecular Formula: C9H18BNO4
• Molecular Weight: 215.057
• Hs Code.: 2933990090
• European Community (EC) Number: 604-696-2
• DSSTox Substance ID: DTXSID70376284
• Mol file: 149682-75-7.mol

Synonyms:1-N-Boc-pyrrolidin-2-ylboronic acid;149682-75-7;1-Boc-Pyrrolidine-2-boronic acid;1-(tert-butoxycarbonyl)pyrrolidin-2-yl-2-boronic acid;MFCD02183523;[1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]boronic Acid;2-BORONO-1-PYRROLIDINECARBOXYLIC ACID 1-(1,1-DIMETHYLETHYL) ESTER;1-PYRROLIDINECARBOXYLIC ACID, 2-BORONO-, 1-(1,1-DIMETHYLETHYL) ESTER;{1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl}boronic acid;2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester;(1-(TERT-BUTOXYCARBONYL)PYRROLIDIN-2-YL)BORONIC ACID;C9H18BNO4;1-N-Boc-pyrrolidin-2-ylboronicacid;(1-tert-butoxycarbonylpyrrolidin-2-yl)boronic acid;SCHEMBL4606763;DTXSID70376284;UIIUYLRUCQCTST-UHFFFAOYSA-N;1-boc-pyrrolidin-2-ylboronic acid;(+/-)-1-(T-BUTOXYCARBONYL)-PYRROLIDINE-2-BORONIC ACID;BCP21345;CS-D0287;N-Boc-pyrrolidin-2-yl]boronic Acid;AKOS015919004;AB11497;AC-4705;AM84455;DS-12270;SY039722;4-BIPHENYL-3,5-DICHLORO-ACETICACID;FT-0603950;EN300-105452;J-503658;1-(tert-butoxycarbonyl)pyrrolidin-2-ylboronicacid;1-N-Boc-Pyrrolidin-2-ylboronic acid

Chemical Property of 1-N-Boc-pyrrolidin-2-ylboronic acid

Chemical Property:

• Vapor Pressure: 2.89E-06mmHg at 25°C
• Refractive Index: 1.488
• Boiling Point: 349.226 °C at 760 mmHg
• PKA: 9.94±0.20(Predicted)
• Flash Point: 165.006 °C
• PSA: 70.00000
• Density: 1.15 g/cm³
• LogP: 0.75570
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 215.1328882
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-pyrrolidin-2-ylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1CCCN1C(=O)OC(C)(C)C)(O)O
• Uses: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester is used as a boc-protected cyclic amine so as to used in the preparation of heterocyclic boronic acid compounds.

Technology Process of 1-N-Boc-pyrrolidin-2-ylboronic acid

There total 7 articles about 1-N-Boc-pyrrolidin-2-ylboronic acid 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: 99.0%

hydrogen (1333-74-0) + N-boc-2-pyrroleboronic acid (135884-31-0) → (N-(1,1-dimethylethoxycarbonyl)pyrrolidin-2-yl)boronic acid (149682-75-7,149716-78-9)

Guidance literature:

With catalyst: PtO₂; In ethyl acetate; inert atmosphere; hydrogenation (50 psi, 8 h) of stirred suspn. of B-compd. and Adam's catalyst, reaction mixt. filtration (Celite), pptn. on filtrat concn. (vac.); elem. anal.;

DOI:10.1021/ja9720220

Reference yield: 88.0%

Trimethyl borate (121-43-7,63156-11-6) → (N-(1,1-dimethylethoxycarbonyl)pyrrolidin-2-yl)boronic acid (149682-75-7,149716-78-9)

Guidance literature:

tert-butyl pyrrolidine-1-carboxylate; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 3.5h;

Trimethyl borate; In tetrahydrofuran; cyclohexane; at -78 - 0 ℃;

With hydrogenchloride; In water; pH=3;

Reference yield: 27.0%

tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → (N-(1,1-dimethylethoxycarbonyl)pyrrolidin-2-yl)boronic acid (149682-75-7,149716-78-9)

Guidance literature:

tert-butyl pyrrolidine-1-carboxylate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; at -78 ℃; for 4h;

With Triisopropyl borate; In diethyl ether; at -78 - 20 ℃; Further stages.;

DOI:10.1021/jo0708792

upstream raw materials:

tert-butyl pyrrolidine-1-carboxylate

Trimethyl borate

hydrogen

N-boc-2-pyrroleboronic acid

Downstream raw materials:

(±)-tert-butyl 2-(3-phenylpropanoyl)pyrrolidine-1-carboxylate

Refernces

• 1、 Batsanov, Andrei S.,Grosjean, Christophe,Schuetz, Thorben,Whiting, Andrew. "A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties". . p. 6276 - 6279. Retrieved 2007.
• 2、 -. "Proline boric acid compound and preparation method and applications thereof". Paragraph 0040; 0041. . Retrieved 2019/01/06.