Aluminium lithium hydride → 2-(4-Aminomethyl-3-fluoro-phenyl)-propan-2-ol

To a stirred solution of 2-fluoro-4-(1-hydroxy-1-methyl-ethyl)-benzonitrile (1.95 g, 11.0 mmol) in tetrahydrofuran (30 mL) at 0° C. was added drop-wise a 1.0 M solution of lithium aluminium hydride in tetrahydrofuran (34 mL, 34.0 mmol). The reaction mixture was warmed to ambient temperature then refluxed for 30 minutes. The reaction mixture was cooled to 0° C., then quenched with methanol (20 mL) added drop-wise. The reaction mixture was then diluted with chloroform (700 mL) and washed with water (100 mL). The resulting suspension was filtered through Celite, after which the organic extract contained in the filtrate was separated, dried over magnesium sulfate (MgSO4), and concentrated to give 1.6 g 2-(4-aminomethyl-3-fluoro-phenyl)-propan-2-ol as an amber gum.

1. temperaturethen refluxed for 30 minutes
2. temperatureThe reaction mixture was cooled to 0° C.
3. customquenched with methanol (20 mL)
4. additionadded drop-wise
5. additionThe reaction mixture was then diluted with chloroform (700 mL)
6. washwashed with water (100 mL)
7. filtrationThe resulting suspension was filtered through Celite
8. extractionafter which the organic extract
9. customwas separated
10. dry with materialdried over magnesium sulfate (MgSO4)
11. concentrationconcentrated

ORD record

ord-1c17d6bae7194284991b4609fe47097b

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06740655B2