Sodium Hydroxide → HCID 58118607, compound

Participants

Reaction Steps

A 4-mL vial with stir bar was charged with methyl 2-(2-methoxypropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxylate (16 mg, 0.061 mmol), methanol (450 μL) and 4M sodium hydroxide (150 μL, 0.61 mmol). The mixture was stirred at room temperature for 1 hour then quenched into 1M NaH2PO4 (2 mL) and 1M citric acid was added to obtain pH 4-5. The mixture was extracted with EtOAc (3 mL×3), dried (Na2SO4), filtered and evaporated to obtain a colorless oil (24 mg), which was used directly in the next step. m/z=250.3 (M+H)+. 1H NMR (400 MHz; CD3OD) δ 8.32 (d, J=8.3 Hz, 1H), 7.83 (d, J=8.3 Hz, 1H), 3.3.0 (s, 3H), 3.29-3.15 (m, 4H), 3.00-2.90 (m, 1H), 2.41-2.31 (m, 1H), 2.17-2.04 (m, 1H), 2.04 (s, 2H), 1.66 (s, 6H).

Provenance & Evidence