Lithium hydroxide, monohydrate → HCID 67085566, compound

Participants

Reaction Steps

To a solution of the product from step E (8.51 g, 15.23 mmol) in tetrahydrofuran (102 mL) and MeOH (51 mL) was added a solution of lithium hydroxide monohydrate (1.92 g, 45.69 mmol) in water (25 mL) at ambient temperature. The mixture was stirred vigorously for 2.5 h, quenched with aqueous saturated NH4Cl solution (75 mL), and extracted with ethyl acetate (2×200 mL). The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexane/ethyl acetate, 70:30) to afford (+)-tert-butyl 2-bromo-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (5.29 g, 92%) as a white solid: [α]D=+142.4° (c 0.33, MeOH); 1H NMR (CDCl3, 300 MHz) δ 7.93 (s, 1H), 7.61 (d, J=0.9 Hz, 1H), 7.11-7.23 (dd, J=16.8, 8.4 Hz, 2H), 5.14 (s, 1H), 4.65 (s, 1H), 3.28-3.57 (m, 1H), 2.47 (d, J=16.2 Hz, 1H), 2.10-2.38 (m, 2H), 1.88-1.98 (m, 1H), 1.54-1.70 (m, 1H), 1.38 (s, 9H).

Provenance & Evidence