Water → HCID 22219610, compound

Participants

Reaction Conditions

Reaction Steps

Under N2, a flame-dried, 100-mL, three-necked flask was charged with lithium borohydride (0.39 g, 17.0 mmol) and anhydrous THF (10 mL) and cooled to −10° C. A solution of tert-butyl 1-(2-ethoxy-2-oxoethyl)-6,7,9,10-tetrahydroazepino[4,5-g]indole-8(1H)-carboxylate (2.11 g, 5.66 mmol) in anhydrous THF (20 mL) was added and the mixture was allowed to warm to room temperature and was stirred for 2 hours. An additional equivalent of lithium borohydride (0.13 mL, 5.66 mmol) was added and the mixture was stirred at room temperature for 16 hours. Water was added slowly and the mixture was partitioned between EtOAc and water. The combined organic layers were concentrated to give 2.09 g of an oil. Column chromatography (elution with 10–30% Et2O/hexane) gave 1.70 g (91%) of the title compound as a clear oil. An analytical sample was crystallized from EtOAc hexane to give a white solid: mp 109–111° C.; 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=8 Hz, 1 H), 7.03 (d, J=3 Hz, 1 H), 6.90 (d, J=8 Hz, 1 H), 6.45 (d, J=3 Hz, 1 H), 4.45 (t, J=5 Hz, 2 H), 3.99–3.88 (m, 2 H), 3.72–3.54 (m, 4 H), 3.39–3.25 (m, 2 H), 3.10–2.99 (m, 2 H), 1.38 (s, 9 H); IR (diffuse reflectance) 3470, 2976, 1666, 1457, 1428, 1369, 1350, 1312, 1267, 1251, 1192, 1178, 1081, 816, 720 cm−1; MS (EI) m/z 330 (M+); Anal. Calcd for C19H26N2O3: C, 69.06; H, 7.93; N, 8.48. Found: C, 68.92; H, 7.94; N, 8.43.

Provenance & Evidence