Aluminium lithium hydride → 1-[1-(4-Fluorophenyl)cyclopropyl]methanamine

LAH powder (0.153 g, 4.02 mmol) was added portionwise to a solution of 1-(4-fluorophenyl)cyclopropane carboxamide (0.6 g, 3.35 mmol) in THF (10 mL) at rt and the resulting mixture was heated to reflux for 1 h. The suspension was cooled to rt, quenched with MeOH (2 mL), and then 1N HCl (2 mL). The mixture was filtered through Celite, and the Celite washed with 1N HCl (2 mL). The filtrate was made basic with 50% NaOH, and extracted with EtOAc (3×10 mL). The organic extracts were washed with brine, dried over potassium carbonate, and concentrated. The residue was purified by silica gel chromatography using 0-20% 2M ammonia in MeOH/EtOAc as the eluent to give (1-(4-fluorophenyl)cyclopropyl)methanamine (0.5 g, 2.72 mmol, 81% yield) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.35-7.22 (m, 2H), 7.04-6.92 (m, 2H), 2.75 (s, 2H), 1.15 (br. s., 2H), 0.84-0.68 (m, 4H). LCMS: m+1=166.0.

1. temperaturethe resulting mixture was heated
2. temperatureto reflux for 1 h
3. customquenched with MeOH (2 mL)
4. filtrationThe mixture was filtered through Celite
5. washthe Celite washed with 1N HCl (2 mL)
6. extractionextracted with EtOAc (3×10 mL)
7. washThe organic extracts were washed with brine
8. dry with materialdried over potassium carbonate
9. concentrationconcentrated
10. customThe residue was purified by silica gel chromatography

ORD record

ord-d54563d0310b4176ba6350b4d0d415a8

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765767B2