Methyl iodide → HCID 15082742, compound

HRID 439839Notes

Reaction equation

HRID 439839 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C@@H:7]3[C:12]4[C:17]([CH2:18][C@@H:6]3[C:5]=2[CH:4]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4.I[CH3:20].[H-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:20])[C@@H:7]3[C:12]4[C:17]([CH2:18][C@@H:6]3[C:5]=2[CH:4]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15082735HCID 15082735, compound

Product 1

HCID 15082742HCID 15082742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the same procedure as described in Example 2 for cis-4b,5,9b,10-tetrahydro-8-methoxyindeno[1,2-b]indole (239 mg, 1.0 mmol) was methylated with iodomethane, using sodium hydride (25 mg, 1.1 mmol) as the base, in THF (2 cm3). Extraction work-up (into diethylether), and purification by "suction" flash chromatography, yielded a clear gum. Yield: 158 mg, (63%) which solidified after bulb to bulb distillation (180° C. at 0.2 mm Hg), giving the title compound M.p. 72° C. 1H NMR (CDCl3) δ: 2.87 (3H, s,), 3.03 (1H, dd,), 3.36 (1H, dd,), 3.70 (3H, s,), 4.08 (1H, ddd,), 4.80 (1H, d,), 6.28 (1H, d,), 6.61 (1H, dd,), 6.77 (1H, dd,), 7.1-7.5 (4H, m,).

Workup

  1. extractionExtraction work-up (into diethylether), and purification by "suction" flash chromatography
  2. customyielded a clear gum
  3. distillationto bulb distillation (180° C. at 0.2 mm Hg)

Sources & evidence

ORD record
ord-d1dde87c9af24bddb25b17e5b1e0740a
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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