Triethylamine → (4-{[(Cyclopentanecarbonyl)amino]methyl}phenyl)boronic acid

HRID 1965966Notes

Reaction equation

HRID 1965966 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH:20]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1>C(Cl)Cl>[CH:20]1([C:25]([NH:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([B:10]([OH:12])[OH:11])=[CH:8][CH:9]=2)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 27343114-Aminomethylphenylboronic acid hydrochloride

Product 1

HCID 59787407(4-{[(Cyclopentanecarbonyl)amino]methyl}phenyl)boronic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-aminomethylphenyl boronic acid hydrochloride (1.0 g, 5.34 mmol) in DCM (50 mL), add triethylamine (1.64 mL, 11.74 mmol) and cool the mixture to 0° C. Add cyclopentanecarbonyl chloride (778 mg, 5.78 mmol) and warm to room temperature. Stir the reaction mixture for 18 h, filter and wash the solid with DCM (10 mL) to give the title compound as a fine white powder (1.1 g, 83%).

Workup

  1. filtrationfilter
  2. washwash the solid with DCM (10 mL)

Sources & evidence

ORD record
ord-e3e48b2f18274d179dfb715f3aa41fbf
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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