Water → HCID 12696796, compound

HRID 439837Notes

Reaction equation

HRID 439837 reaction equation
[H-].[Na+].[CH:3]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:4]=1[CH2:5][C@@H:6]1[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C@@H:7]12.I[CH3:20].O>O1CCCC1>[CH3:20][N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C@H:6]2[CH2:5][C:4]3[C:15]([C@@H:7]12)=[CH:16][CH:17]=[CH:18][CH:3]=3

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15082726HCID 15082726, compound

Product 1

HCID 12696796HCID 12696796, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flame dried flask was charged with sodium hydride (60 mg, 2.5 mmol), and tetrahydrofuran (THF) (5 cm3) protected under an atmosphere of nitrogen. To the stirring suspension was added cis-4b,5,9b,10-tetrahydroindeno[1,2-b]indole (500 mg, 2.4 mmol) in THF (5 cm3) dropwise. The reaction was stirred for 1 hour, a pink colour developing. Iodomethane (0.2 cm3) was added, and the solution was stirred overnight. Water (5 cm3) was added, and the THF removed in vacuo. The colourless solid thus obtained was filtered, and dried in a vacuum desiccator. The product was dissolved in 5% ethyl acetate petrol (60°-80° C.) and filtered through a pad of flash silica. After evaporation of the solvent in vacuo, the title compound was obtained as a colourless solid. Yield: 450 mg (85%). M.p. 76°-77° C. 1H NMR (CDCl3) δ: 3.0 (3H, s,), 3.1 (1H, dd,), 3.4 (1H, dd,), 4.1 (1H, ddd,), 4.9 (1H, d,), 6.4 (1H, d,), 6.7 (1H, dd,), 7.1-7.5 (6H, m,).

Workup

  1. customA flame dried flask
  2. stirringthe solution was stirred overnight
  3. customthe THF removed in vacuo
  4. customThe colourless solid thus obtained
  5. filtrationwas filtered
  6. customdried in a vacuum desiccator
  7. dissolutionThe product was dissolved in 5% ethyl acetate petrol (60°-80° C.)
  8. filtrationfiltered through a pad of flash silica
  9. customAfter evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-4e932f8869544e9ba489a2471941aa97
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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