Methanol → cis-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine

Participants

Reaction Steps

Step C (3): cis-N-(3-(Allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide (650 mg, 2.06 mmol) from stepC (2), potassium carbonate (1.42 g, 10.3 mmol) and MeOH (70 mL)/H2O (4.4 mL) were heated at reflux for 7 h. The reaction mixture was concentrated in vacuo. Added water to the residue, extracted with EtOAc, washed the organic layers with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 450 mg (99% yield) of cis-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine as a light brown oil: LC-MS (M+H)+=220.2; 1H NMR (500 MHz, DMSO-d6) δ 7.19 (d, J=8.24 Hz, 1H), 6.97 (d, J=2.14 Hz, 1H), 6.78 (dd, J=8.24, 2.44 Hz, 1H), 5.81-6.07 (m, 1H), 5.30 (dd, J=17.09, 1.83 Hz, 1H), 5.15 (dd, J=10.53, 1.68 Hz, 1H), 4.72 (t, J=6.87 Hz, 1H), 4.02-4.21 (m, 2H), 3.96 (t, J=7.48 Hz, 1H), 3.73 (s, 3H), 2.64-2.88 (m, 1H), 1.39-1.58 (m, 1H).

Provenance & Evidence