Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-2,5-dihydro-1H-pyrrole-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-2,5-dihydro-1H-pyrrole-1-carboxylate
• CAS No.: 212127-83-8
• Molecular Formula: C15H26BNO4
• Molecular Weight: 295.187
• Hs Code.: 2934999090
• European Community (EC) Number: 837-853-0
• DSSTox Substance ID: DTXSID90578748
• Nikkaji Number: J994.252A
• Wikidata: Q72449160
• Mol file: 212127-83-8.mol

Synonyms:212127-83-8;TERT-BUTYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2,5-DIHYDRO-1H-PYRROLE-1-CARBOXYLATE;1-BOC-2,5-Dihydro-1H-pyrrole-3-boronic acid, pinacol ester;tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydropyrrole-1-carboxylate;tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate;1-BOC-2,5-Dihydro-1H-pyrrole-3-boronic acid pinacol ester;MFCD10697918;3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester;tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate;2,5-Dihydro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylic Acid 1,1-Dimethy;C15H26BNO4;OIZXJJIHVIYNKZ-UHFFFAOYSA-N;SCHEMBL1763807;1-Boc-2,5-dihydropyrrole-3-boronic Acid Pinacol Ester;DTXSID90578748;BCP10055;N-BOC-2,5-DIHYDRO-1H-PYRROLE-3-BORONIC ACID PINACOL ESTER;AKOS015946357;AB60818;AM85103;CS-W008634;(1-(TERT-BUTOXYCARBONYL)-2,5-DIHYDRO-1H-PYRROL-3-YL)BORONIC ACID PINACOL ESTER;1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester;2,5-DIHYDRO-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRROLE-1-CARBOXYLIC ACID, TERT-BUTYL ESTER;DS-14119;SY008437;EN300-171007;A852979;Z1495100563;2,5-Dihydro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester;TERT-BUTYL3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2,5-DIHYDRO-1H-PYRROLE-1-CARBOXYLATE

Chemical Property of Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-2,5-dihydro-1H-pyrrole-1-carboxylate

Chemical Property:

• Boiling Point: 330.5±52.0 °C(Predicted)
• PKA: -1.18±0.40(Predicted)
• PSA: 48.00000
• Density: 1.06±0.1 g/cm3(Predicted)
• LogP: 2.73280
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 295.1954885
• Heavy Atom Count: 21
• Complexity: 449

Purity/Quality:

99%, ^*data from raw suppliers

2,5-Dihydro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCN(C2)C(=O)OC(C)(C)C
• Uses: 1-Boc-2,5-Dihydro-1H-pyrrole-3-boronic acid, pinacol ester can be used in the synthesis of series of kinase inhibitors.

Technology Process of Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-2,5-dihydro-1H-pyrrole-1-carboxylate

There total 10 articles about Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-2,5-dihydro-1H-pyrrole-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: 85.0%

tert-butyl allyl[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-allyl]carbamate (212127-74-7) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydropyrrole-1-carboxylate (212127-83-8)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.202000977

Reference yield: 81.0%

3-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester (630121-86-7) + bis(pinacol)diborane (73183-34-3) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydropyrrole-1-carboxylate (212127-83-8)

Guidance literature:

With potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

Reference yield:

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (101385-93-7) + bis(pinacol)diborane (73183-34-3) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydropyrrole-1-carboxylate (212127-83-8) + tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate (1401165-14-7)

Guidance literature:

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.333333h;

With N,N-phenylbistrifluoromethane-sulfonimide; In tetrahydrofuran; at 20 ℃; for 1h;

bis(pinacol)diborane; With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Overall yield = 86 %; Overall yield = 800 g;

upstream raw materials:

tert-butyl allyl[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-allyl]carbamate

3-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester

bis(pinacol)diborane

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

Downstream raw materials:

tert-butyl 3-(1-(4-methoxybenzyl)-4-(2-(4-methylpyrimidin-2-ylamino)thiazol-4-yl)-1H-pyrazol-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

3-(4-carboxy-2-trifluoromethyl-phenyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

3-(4-carboxy-2-trifluoromethyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

1-tert-butoxycarbonyl-3-(3-hydroxyphenyl)pyrrolidine

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