Potassium Carbonate → (S)-N-(2-Methoxyethyl)-3-methyl-1-(pyrrolidin-1-yl)butan-2-amine

(S)-3-Methyl-1-(pyrrolidin-1-yl)butan-2-amine (0.24 g, 1.54 mmol), which is commercially available, and potassium carbonate (0.139 mL, 2.30 mmol) was slurried in MeCN. 1-Bromo-2-methoxyethane (0.147 mL, 1.54 mmol) was added and the reaction was stirred at rt for 2 h. LMCS showed only traces of the desired product. DIPEA (0.535 mL, 3.07 mmol) was added and the resultant mixture was stirred at rt over night and heated at 60° C. for 4 h. The mixture was cooled to rt and diluted with water (50 mL) and DCM (50 mL). The two layers were separated and the water layer was extracted with DCM (3×100 mL). The organic layers were combined and washed with brine (100 mL), passed through phase separator and concentrated under reduced pressure to give the title compound (0.31 g, 97%). The obtained crude product was used without further purification. LCMS (M+H)+: 215.

ORD record

ord-fcff5d1ea3784c03a1a1d6d54253a65b

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2