Acetic Acid → 4-[(S)-1-(4-Bromo-phenyl)-ethylamino]-1-methoxy-2-phenyl-butan-2-ol

(S)-1-(4-Bromo-phenyl)-ethylamine (0.93 g), NaB(OAc)3 (0.98 g), and acetic acid (0.27 mL) were added in the given order to a solution of 3-hydroxy-4-methoxy-3-phenyl-butyraldehyde (0.90 g) in tetrahydrofuran (20 mL) at ca. 10-15° C. The cooling bath was removed and the mixture was stirred at room temperature for 2 h. Then, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added and the resulting mixture was stirred for another 30 min. The mixture was extracted with ethyl acetate and the combined extracts were washed with water and brine. After drying (MgSO4), the solvent was removed to give the title compound which was submitted to the subsequent reaction step without further purification. Yield: 1.80 g (quantitative). Mass spectrum (ESI+): m/z=378/380 (Br) [M+H]+

1. customThe cooling bath was removed
2. additionThen, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added
3. stirringthe resulting mixture was stirred for another 30 min
4. extractionThe mixture was extracted with ethyl acetate
5. washthe combined extracts were washed with water and brine
6. dry with materialAfter drying (MgSO4)
7. customthe solvent was removed

ORD-Eintrag

ord-1c209d81b068442eab848c615b4312c5

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08569292B2