Methylamine → (2R)-(4E)-N-Methyl-5-(3-pyridyl)-4-penten-2-amine

Temperature

105 °C

A mixture of (2S)-(4E)-5-(3-pyridyl)-4-penten-2-ol p-toluenesulfonate (3.80 g, 11.97 mmol) and methylamine (20 mL, 2.0M solution in THF) was heated at 100-110° C. for 8 h in a sealed glass tube. The mixture was cooled to ambient temperature and concentrated under reduced pressure on a rotary evaporator. The resulting brown syrup was diluted with saturated NaHCO3 solution (25 mL) and extracted with chloroform (4×25 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation to afford a thick, brown syrup (2.00 g). The crude product was purified by column chromatography on silica gel, eluting with chloroform-methanol (95:5, v/v). Selected fractions were combined, concentrated by rotary evaporation affording a 800 mg (37.9%) of a pale-yellow oil.

1. temperatureThe mixture was cooled to ambient temperature
2. concentrationconcentrated under reduced pressure on a rotary evaporator
3. additionThe resulting brown syrup was diluted with saturated NaHCO3 solution (25 mL)
4. extractionextracted with chloroform (4×25 mL)
5. dry with materialThe combined chloroform extracts were dried (K2CO3)
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation

ORD record

ord-c1f47da3d71b446ca9c2f525bf45ecc5

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06979695B2