Water → HCID 22219610, compound

HRID 1793806Notes

Reaction equation

HRID 1793806 reaction equation
[BH4-].[Li+].C([O:5][C:6](=O)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17][C:15]3=2)[CH:10]=[CH:9]1)C.O>C1COCC1>[OH:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17][C:15]3=2)[CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydride2×HCID 22219598HCID 22219598, compound

Product 1

HCID 22219610HCID 22219610, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

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.

Workup

  1. temperatureto warm to room temperature
  2. stirringthe mixture was stirred at room temperature for 16 hours
  3. customthe mixture was partitioned between EtOAc and water
  4. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-373cc6e4d47146d6adf1800c1e1091ea
Source dataset
uspto-grants-2006_04
Patent number
US07022694B2

Reaction notes

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