Background and overview[1]
3-Hydroxymethylphenylboronic acid pinacol ester can be used as a pharmaceutical synthesis intermediate. If 3-Hydroxymethylphenylboronic acid pinacol ester is inhaled, move the patient to fresh air; if skin contact occurs, remove contaminated clothing and rinse skin thoroughly with soap and water. If discomfort occurs , seek medical attention; if eye contact occurs, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.
Structure
Apply[1]
3-Hydroxymethylphenylboronic acid pinacol ester can be used as an intermediate for pharmaceutical and chemical synthesis. For example, it can be used to prepare a reactive oxygen species (ROS)-sensitive cyclodextrin material as a drug delivery carrier. Specifically The steps are: under nitrogen protection, 10 mmol of 3-hydroxymethylphenylboronic acid and 15mmol of pinacol are reacted in 60 mL of anhydrous tetrahydrofuran to obtain 3-hydroxymethylphenylboronic acid pinacol ester; 5mmol of 3-hydroxymethylphenylboronic acid pinacol ester. React with 10 mmol N, N’-carbonyldiimidazole in 20 mL anhydrous chloroform to obtain 3-imidazole carbonyloxy-phenylboronic acid pinacol ester; in the presence of 4 mmol 4-dimethylaminopyridine, 0.3 mmol α-cyclodextrin and 4 mmol of 3 -Imidazole carbonyloxy-phenylboronic acid pinacol ester was reacted in 15 mL of dimethyl sulfoxide at 20°C. After 8 hours, the cyclodextrin material was obtained by precipitating in water, collecting by centrifugation, and drying.
Preparation[2]
The preparation of 3-hydroxymethylphenylboronic acid pinacol ester is as follows:
To a suspension of LiAlH4 (100 mg, 2.63 mmol) in THF (30 mL) was added portionwise 3-(4,4,5,5-tetramethyl-1,3,2-dioxa Borolane-2-methyl)benzoic acid (100 mg, 0.76 mmol). The reaction mixture was stirred at room temperature for an additional 3 hours. H2O (3 mL) was added dropwise at 0°C, then the mixture was filtered and concentrated under reduced pressure to obtain crude product (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) Alk-2-yl)phenyl)methanol (3-hydroxymethylphenylboronic acid pinacol ester, 190 mg).
Main reference materials
[1] CN103755839 Active oxygen free radica Clariant dye l sensitive cyclodextrin materialas drug delivery carrierand preparation method thereof
[2] WO2012163724 TRIAZOLOPYRIDINE COMPOUNDS
