Methylamine → 1198225-51-2

1-Phenylcyclopropanecarboxylic acid (2.95 g) was dissolved in DMF (120 mL). To the solution, EDC.HCl (5.2 g), HOBt (3.2 g), and a solution of methylamine in methanol (40%, 1.94 mL) were added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (50% ethyl acetate/hexane). An aliquot (1.1 g) of the obtained amide compound (2.9 g) was dissolved in THF (60 mL). To the solution, a solution of LAH in THF (2.4 M, 7.9 mL) was added dropwise at 0° C., and the mixture was heated to reflux at 80° C. for 12 hours. To the reaction mixture, water (4.0 mL) was gradually added dropwise at 0° C. The precipitate was removed by filtration and washed with THF (60 mL). Then, the combined filtrate was concentrated under reduced pressure to obtain the title compound (1.0 g) as a colorless oil.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. customthe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)
3. dissolutionAn aliquot (1.1 g) of the obtained amide compound (2.9 g) was dissolved in THF (60 mL)
4. additionTo the solution, a solution of LAH in THF (2.4 M, 7.9 mL) was added dropwise at 0° C.
5. temperaturethe mixture was heated
6. temperatureto reflux at 80° C. for 12 hours
7. additionTo the reaction mixture, water (4.0 mL) was gradually added dropwise at 0° C
8. customThe precipitate was removed by filtration
9. washwashed with THF (60 mL)
10. concentrationThen, the combined filtrate was concentrated under reduced pressure

ORD 기록

ord-f6bc5e03c5a04fc3b945c958532c1f0d

출처 데이터셋

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08530490B2