Methanol → (1R)-2-Allyloxy-1-phenyl-ethanamine

Participants

Reaction Steps

Step Q (3): (R)-N-(2-(Allyloxy)-1-phenylethyl)-2,2,2-trifluoroacetamide (3.0 g, 11.0 mmol) from step Q (2), potassium carbonate (7.59 g, 55 mmol), methanol (300 mL) and H2O (20 mL) were heated to reflux for 16 h. The mixture was concentrated in vacuo. Water was added, and the aqueous layer was repeatedly extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo to afford 1.06 g (54% yield) of (R)-2-(allyloxy)-1-phenylethanamine as a yellow oil. The crude mixture was used without further purification. LC-MS (M+H)+=178.18. 1H NMR (300 MHz, CDCl3) δ ppm 2.02 (s, 2H) 3.38 (t, J=9.15 Hz, 1H) 3.48-3.63 (m, 1H) 3.99 (d, J=5.49 Hz, 2H) 4.19 (dd, J=9.15, 3.66 Hz, 1H) 5.05-5.31 (m, 2H) 5.74-5.99 (m, 1H) 7.15-7.42 (m, 5H).

Provenance & Evidence