反应 #1880988

反应方程式

Water

lithium borohydride

tert-butyl 1-(2-ethoxy-2-oxoethyl)-6,7,9,10-tetrahydroazepino[4,5-g]indole-8(1H)-carboxylate

lithium borohydride

→

oil

收率 111.8%

tert-Butyl 1-(2-hydroxyethyl)-6,7,9,10-tetrahydroazepino[4,5-g]indole-8(1H)-carboxylate

收率 111.8%

溶剂

THF

THF

反应条件

后处理

1. 1
   温度to warm to room temperature
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 16 hours
3. 3
   其他the mixture was partitioned between EtOAc and water
4. 4
   浓缩The combined organic layers were concentrated

实验过程

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.

来源