Hydride → HCID 10020923, compound

HRID 1071022Notes

Reaction equation

HRID 1071022 reaction equation
[Li].[H-].[C:3]([N:11]1[CH2:24][CH2:23][C:22]2[C:21]3[CH:20]=[CH:19][C:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:17][C:16]=3[NH:15][C:14]=2[CH2:13][CH2:12]1)(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CCOC(C)=O.CCCCCCC>O1CCCC1>[CH2:3]([N:11]1[CH2:24][CH2:23][C:22]2[C:21]3[CH:20]=[CH:19][C:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:17][C:16]=3[NH:15][C:14]=2[CH2:13][CH2:12]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 166653HydrideHCID 3028194LithiumHCID 21899848Ethylacetate heptaneHCID 22396658HCID 22396658, compound

Product 1

HCID 10020923HCID 10020923, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium alunmnum hydride (1.40 g, 36.9 mmol) in tetrahydrofuran (15.0 mL) and a solution of 3-benzoyl-8-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (1.40 g, 3.82 mmol) in tetrahydrofuran (30.0 mL) at 0° C. were reacted in a manner similar to Example 1 to give an oil. Column chromatography (silica gel, 20-30% EtOAc/heptane) afforded 1.22 g (90%) of the title compound as a white solid: mp 176-177° C.; 1H NMR (400 MHz, CDCl3) δ 7.74, 7.63-7.61, 7.48, 7.45-7.40, 7.36, 3.84, 3.00-2.92; 13C NMR (100 MHz, CDCl3) δ 142.5, 139.3, 136.9, 135.2, 134.5, 128.9, 128.6, 128.5, 128.3, 127.3, 127.0, 126.4, 119.1, 117.8, 112.8, 108.8, 60.7, 55.7, 53.8, 28.6, 23.9; IR (drift) 3385, 3371, 1467, 1344, 1328, 1120, 1027, 870, 820, 765, 756, 750, 735, 728, 698 cm−1; MS (EI) m/z 352 (M+); Anal. Calcd for C25H24N2: C, 85.19; H, 6.86; N, 7.95. Found: C, 85.24; H, 6.89; N, 8.05.

Workup

  1. customto give an oil

Sources & evidence

ORD record
ord-b355a91701214c1987a831c5fbc9dbff
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

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