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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 336573Generated: October 26, 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/336573

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 numberUS08889675B2
Source datasetuspto-grants-2014_11
ORD IDord-63ff3c89dfbb4fed8261f7af31e51bea
Source noteuspto-grants-2014_11