1-Boc-pyrrolidine-3-boronic acid pinacol ester

Base Information

• Chemical Name: 1-Boc-pyrrolidine-3-boronic acid pinacol ester
• CAS No.: 1312712-22-3
• Molecular Formula: C₁₅H₂₈BNO₄
• Molecular Weight: 297.203
• Hs Code.: 2934999090
• Mol file: 1312712-22-3.mol

Synonyms:1-Boc-pyrrolidine-3-boronic acid pinacol ester;tert-Butyl 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate

Chemical Property of 1-Boc-pyrrolidine-3-boronic acid pinacol ester

Chemical Property:

• Boiling Point: 341.6±35.0 °C(Predicted)
• PKA: -1.00±0.40(Predicted)
• PSA: 48.00000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 3.02750

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-Pyrrolidine-3-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Boc-pyrrolidine-3-boronic acid pinacol ester

There total 4 articles about 1-Boc-pyrrolidine-3-boronic acid pinacol ester 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: 81.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) + 1-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate → tert-butyl (R)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate (1312712-22-3)

Guidance literature:

2,2'-bis(1,3,2-benzodioxaborole); 1-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate; In N,N-dimethyl acetamide; for 6h; Schlenk technique; Inert atmosphere; Irradiation;

2,3-dimethyl-2,3-butane diol; With triethylamine; at 20 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201804246

Reference yield: 63.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 3-bromopyrrolidine-1-carboxylic acid tert-butyl ester (939793-16-5,569660-97-5) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) → C15H28BNO4 (1312712-22-3)

Guidance literature:

3-bromopyrrolidine-1-carboxylic acid tert-butyl ester; 2,2'-bis(1,3,2-benzodioxaborole); With tetrabutylammonium tetrafluoroborate; In N,N-dimethyl acetamide; at 25 ℃; for 0.316667h; Electrolysis; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; With triethylamine; In N,N-dimethyl acetamide; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.1c06473

Reference yield: 62.0%

tert-butyl pyrrolidine-1-carboxylate (86953-79-9) + bis(pinacol)diborane (73183-34-3) → C15H28BNO4 (1312712-22-3)

Guidance literature:

With 2-methyl-1,10-phenanthroline; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In Cyclooctan; at 100 ℃; Concentration; regioselective reaction; Sealed tube;

DOI:10.1126/science.aba6146

upstream raw materials:

3-amino-1-(t-butoxycarbonyl)pyrrolidine

2,3-dimethyl-2,3-butane diol

2,2'-bis(1,3,2-benzodioxaborole)

tert-butyl pyrrolidine-1-carboxylate

Downstream raw materials:

tert-butyl 3-fluoropyrrolidine-1-carboxylate

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine

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