Sodium hydride → HCID 67085779, compound

Participants

Reaction Steps

To a solution of the product of Example 88, step C (120 mg, 0.27 mmol) in anhydrous DMF (3 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 22 mg, 0.54 mmol), tetrabutylammonium iodide (51 mg, 0.13 mmol) and 18-crown-6 (7 mg, 0.02 mmol). The resulting mixture was stirred for 30 min before 2-bromoethoxy-tert-butyldimethylsilane (0.07 ml, 0.32 mmol) was added. The reaction mixture was stirred at room temperature for 4 h, quenched with water and extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered, and concentrated to give tert-butyl 2-phenylsulfonyl-5-[2-(tert-butyldimethylsilyloxy)]ethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (160 mg, quant) as a yellow-brown solid: 1H NMR (CDCl3, 300 MHz), δ 8.39 (s, 1H), 8.14-8.18 (m, 2H), 7.86 (d, J=8.4 Hz, 1H), 7.63-7.71 (m, 3H), 7.56 (d, J=8.7 Hz, 1H), 5.47 (br s, 1H), 4.91 (br s, 1H), 4.25-4.38 (m, 2H), 4.03 (t, J=5.4 Hz, 2H), 2.76 (d, J=16.2 Hz, 1H), 2.34-2.57 (m, 2H), 2.10-2.22 (m, 1H), 1.79-1.86 (m, 2H), 1.58 (s, 9H), 0.93 (s, 9H), 0.04 (s, 3H), 0.01 (s, 3H).

Provenance & Evidence