tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate
• CAS No.: 1048970-17-7
• Molecular Formula: C16H30BNO4
• Molecular Weight: 311.229
• Hs Code.: 2934999090
• Mol file: 1048970-17-7.mol

Synonyms:tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate

Chemical Property of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate

Chemical Property:

• Melting Point: 60-65°C
• Boiling Point: 358.8 °C at 760 mmHg
• PKA: -1.07±0.40(Predicted)
• Flash Point: 170.8 °C
• PSA: 48.00000
• Density: 1.03 g/cm³
• LogP: 3.41760
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

N-Boc-piperidine-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 1-Boc-piperidin-4-ylboronic acid, pinacol ester

Technology Process of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate

There total 2 articles about tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-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: 58.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) + tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate (1612172-49-2) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylic acid tert-butyl ester (1048970-17-7) + bis(pinacol)diborane (73183-34-3)

Guidance literature:

2,2'-bis(1,3,2-benzodioxaborole); tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate; With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In N,N-dimethyl acetamide; for 24h; Inert atmosphere; Schlenk technique; Irradiation;

2,3-dimethyl-2,3-butane diol; With triethylamine; In N,N-dimethyl acetamide; for 2h; Inert atmosphere; Schlenk technique; Irradiation;

DOI:10.1002/anie.201904028

Reference yield:

t-butyl piperidinecarboxylate (75844-69-8) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylic acid tert-butyl ester (1048970-17-7) + C16H30BNO4

Guidance literature:

With 2-methyl-1,10-phenanthroline; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In Cyclooctan; at 100 ℃; Overall yield = 41 percent; regioselective reaction; Inert atmosphere;

DOI:10.1126/science.aba6146

Reference yield: 99.0%

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylic acid tert-butyl ester (1048970-17-7) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine hydrochloride (1218790-99-8)

Guidance literature:

With sulfuric acid; sodium chloride; In neat (no solvent); at 20 ℃; for 4h; Sealed tube; Inert atmosphere;

DOI:10.1039/d1ob00728a

upstream raw materials:

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

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

tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate

t-butyl piperidinecarboxylate

Downstream raw materials:

1-tert-butoxycarbonyl-4-cyanopiperidine

tert-butyl 4-ethenylpiperidine-1-carboxylate

6-amino-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Friese, Florian W.,Studer, Armido. "Deoxygenative Borylation of Secondary and Tertiary Alcohols". supporting information. p. 9561 - 9564. Retrieved 2019/06/21.