Sodium Hydroxide → 1-(4-Fluorobenzyl)cyclopropanamine

To a solution of 4-fluorophenyl acetonitrile (2.7 g) in tetrahydrofuran (40 mL) was added tetraisopropoxy titanium (6.5 mL), whereafter a solution of 1.0M magnesium ethylbromide-tetrahydrofuran (40 mL) was added dropwise over 30 minutes, and stirred for 1 hour. After adding a trifluoroborane-diethyl ether complex (50.1 mL) over 20 minutes, the solution was further stirred for 1 hour. The reaction solution was cooled with ice water, an aqueous solution of 5N sodium hydroxide (20 mL) was added, and stirred at room temperature for 20 minutes. After diluting with water and diethyl ether, and filtration using Celite was carried out. The organic layer was separated, washed with saturated sodium chloride water, and then dried with anhydrous sodium sulfate. After the solvent was evaporated at reduced pressure, filtration was carried out using a small amount of NH-silica gel, and washing was carried out with ethyl acetate. The residue that was obtained upon removing the solvent by evaporation was purified by NAM silica gel column chromatography (dichloromethane/methanol), and the title compound (0.75 g) was obtained as a yellow oily substance.

1. additionAfter adding a trifluoroborane-diethyl ether complex (50.1 mL) over 20 minutes
2. stirringthe solution was further stirred for 1 hour
3. stirringstirred at room temperature for 20 minutes
4. customThe organic layer was separated
5. washwashed with saturated sodium chloride water
6. dry with materialdried with anhydrous sodium sulfate
7. customAfter the solvent was evaporated at reduced pressure, filtration
8. washwashing
9. customThe residue that was obtained
10. customupon removing the solvent
11. customby evaporation
12. customwas purified by NAM silica gel column chromatography (dichloromethane/methanol)

ORDレコード

ord-d45a80f1cbb0434a8e1900df49a98815

出典データセット

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07217723B2