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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 588650Generated: October 30, 2026

Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-1H-pyrazole

https://huagongshe.com/reaction/588650

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 64556—
ReactantCyanomethylenetributylphosphoraneHCID 4622928—
Reactant3,5-Dimethylpyrazole-4-boronic acid, pinacol esterHCID 16217713—
SolventTolueneHCID 1140—
Product3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-1H-pyrazoleHCID 86681254—

Reaction Steps

To a solution of 1-adamantanemethanol (0.090 g), 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.160 g) and cyanomethylenetributylphosphorane (0.215 g) were added and stirred together in toluene (2 mL) at room temperature. After stirring overnight the reaction was loaded directly onto silica gel and eluted using a gradient of 2% to 20% ethyl acetate/hexanes to provide the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09227963B2
Source datasetuspto-grants-2016_01
ORD IDord-d9846638753e423fb48dc9f90247edc0
Source noteuspto-grants-2016_01