Borane;tetrahydrofuran → (3,4-Dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-amine
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=O)[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].B.O1CCCC1>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 390 mg (1.5 mmol) N-(3,4-dimethyl-phenyl)-2-(5-methyl-pyridin-2-yl)-acetamide in 8 mL THF under argon at ambient temperature, was added dropwise 3.1 mL (3.1 mmol) of a 1 M borane-tetrahydrofuran solution. The solution was refluxed for 5 hours, cooled to 0° C. and quenched with 7 mL of a 20% NH4Cl solution. The solution was acidified with HCl 5N and stirred at ambient temperature for 1.5 hours. The residue was basified with a sat. NaHCO3 solution, and concentrated. The residue was dissolved in ethylacetate, the aqueous phase was extracted 2 times with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.038 g (10%) of the title compound as a yellow oil. MS (m/e): 241.3 [M+H]+.
Workup
- temperatureThe solution was refluxed for 5 hours
- customquenched with 7 mL of a 20% NH4Cl solution
- concentrationconcentrated
- dissolutionThe residue was dissolved in ethylacetate
- extractionthe aqueous phase was extracted 2 times with ethyl acetate
- dry with materialThe combined extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
- customformed from heptane and ethylacetate
Sources & evidence
- ORD record
- ord-fa3109e7984946a3bb748c21778eb8a0
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08133909B2
Reaction notes
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