Sodium Hydroxide → 2-Amino-1-(3,4-difluorophenyl)ethan-1-ol

To a solution consisting of 3,4-difluorobenzaldehyde (3.85 g, 27.1 mmol), zinc iodide (104.9 mg, 0.329 mmol) and THF (5 mL) at 0° C. under nitrogen was added TMSCN (4.60 mL, 33.9 mmol). The resultant mixture was stirred for 3.5 h at 0° C. and then cannulated into a 0° C. suspension of LiAlH4 (1.41 g, 67.7 mmol) in THF (80 mL). The resultant mixture was allowed to gradually warm to rt with stirring for 21 h. The reaction mixture was then re-cooled to 0° C. and carefully treated with water (2.57 mL) followed by 15% aq. NaOH (2.57 mL) and lastly with water (7.7 mL). The resultant mixture was stirred for 1 h, the solids removed by vacuum filtration and the filtrate concentrated. The resulting crude product was purified by FCC(CH2Cl2/MeOH/NH3) to give the desired product.

1. customcannulated into a 0° C.
2. temperatureThe reaction mixture was then re-cooled to 0° C.
3. customthe solids removed by vacuum filtration
4. concentrationthe filtrate concentrated
5. customThe resulting crude product was purified by FCC(CH2Cl2/MeOH/NH3)

ORD record

ord-4c36c7ec13bb43329f7bff855482fb31

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598202B2