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

HRID 588650Notes

Reaction equation

HRID 588650 reaction equation
[C:1]12([CH2:11]O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:13][C:14]1[C:18]([B:19]2[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]2)=[C:17]([CH3:28])[NH:16][N:15]=1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[CH3:13][C:14]1[C:18]([B:19]2[O:23][C:22]([CH3:24])([CH3:25])[C:21]([CH3:27])([CH3:26])[O:20]2)=[C:17]([CH3:28])[N:16]([CH2:11][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)[N:15]=1

Participants

5

Reactant 3

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 4622928CyanomethylenetributylphosphoraneHCID 162177133,5-Dimethylpyrazole-4-boronic acid, pinacol ester

Product 1

HCID 866812543,5-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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  1. washeluted

Sources & evidence

ORD record
ord-d9846638753e423fb48dc9f90247edc0
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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