Sodium borohydride → HCID 58266768, compound

Participants

Reaction Steps

Sodium borohydride (260 mg, 6.86 mmol) was added to a cooled (0° C.) solution of 2-ethyl-6,8-dimethoxy-3,4-dihydroisoquinolinium iodide (1.19 g, 3.43 mmol) in methanol (15 mL). On complete addition the mixture was allowed to warm to ambient temperature and stirred for 1.5 h. The mixture was evaporated in vacuo and the resultant residue was partitioned between diethyl ether and water. The organic phase was dried over sodium sulfate, filtered and evaporated to afford the title compound as a yellow oil (741 mg, 98%). 1H NMR (CDCl3, 300 MHz): 6.27 (d, J=2.3 Hz, 1H), 6.24 (d, J=2.3 Hz, 1H), 3.78 (s, 3H), 3.76 (s, 3H), 3.51-3.47 (m, 2H), 2.89-2.83 (m, 2H), 2.71-2.64 (m, 2H), 2.60 (q, J=7.2 Hz, 2H), 1.19 (t, J=7.2 Hz, 3H). LCMS (Method B): RT=1.62 min, M+H+=222.

Provenance & Evidence