Methylamine → (R,E)-5-(5-Isopropoxypyridin-3-yl)-N-methylpent-4-en-2-amine

Temperature

100 °C

A mixture of (2S)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-ol p-toluenesulfonate (10.00 g, 26.63 mmol) and methylamine (50 mL, 2.0M solution in THF) was heated at 100° C. for 10 h in a sealed glass tube. The mixture was cooled to ambient temperature and concentrated under reduced pressure on a rotary evaporator. The crude product was treated with saturated NaHCO3 solution (50 mL) and extracted with chloroform (4×50 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation to afford a dark-brown oil (3.50 g). The crude product was purified by repeated (twice) column chromatography on silica gel, eluting with chloroform-methanol (95:5, v/v). Selected fractions were combined, concentrated by rotary evaporation affording a light-brown oil (2.50 g). The oil was further purified by vacuum distillation using a short-path distillation apparatus, collecting 2.05 g (32.9%) of a colorless oil, bp 98-100° C. at 0.04 mm Hg.

1. temperatureThe mixture was cooled to ambient temperature
2. concentrationconcentrated under reduced pressure on a rotary evaporator
3. additionThe crude product was treated with saturated NaHCO3 solution (50 mL)
4. extractionextracted with chloroform (4×50 mL)
5. dry with materialThe combined chloroform extracts were dried (K2CO3)
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation

ORD record

ord-3bf4bdbc34b64220854f18080260a390

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06232316B1