Methyl iodide → HCID 22861097, compound

HRID 439845Notes

Reaction equation

HRID 439845 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C@@H:8]3[C:13]4[C:18]([CH2:19][C@@H:7]3[C:6]=2[CH:5]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4)([CH3:3])[CH3:2].[H-].[Na+].I[CH3:23]>C1COCC1>[CH3:23][N:9]1[C:10]2[CH:11]=[CH:12][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]=2[C@H:7]2[CH2:19][C:18]3[C:13]([C@@H:8]12)=[CH:14][CH:15]=[CH:16][CH:17]=3

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1229702HCID 1229702, compound

Product 1

HCID 22861097HCID 22861097, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of cis-4b,5,9b,10-tetrahydro-8-isopropylindeno[1,2-b]indole (1.75 g, 7.0 mmol) in THF (10 cm3), was added to a suspension of sodium hydride (200 mg, 1.2 equivalents) in THF (7 cm3), at 0° C. The reaction was stirred for two hours and iodomethane (0.53 cm3, 1.2 equivalents) was added. The reaction was stirred overnight, and then quenched with a saturated solution of ammonium chloride. The organic phase was separated, and the aqueous phase extracted with diethyl ether. The combined organic phases were dried (Na2SO4), and solvent removed in vacuo to yield the title compound as a colourless gum which was purified by bulb to bulb distillation. Yield: 1.0 g (54%). B.p. 200° C. at 0.4 mmHg. 1H NMR (CDCl3) δ: 1.22 (6H, d,), 2.81 (1H, septet,), 2.94 (3H, s,), 3.09 (1H, dd,), 3.43 (1H, dd,), 4.15 (1H, ddd,), 4.90 (1H, d,), 6.32 (1H, d,), 6.93 (1H, dd,), 7.02 (1H, br,), 7.1-7.5 (4H, m,).

Workup

  1. stirringThe reaction was stirred overnight
  2. customquenched with a saturated solution of ammonium chloride
  3. customThe organic phase was separated
  4. extractionthe aqueous phase extracted with diethyl ether
  5. dry with materialThe combined organic phases were dried (Na2SO4), and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-634356333c684b2fb79ed90e6f75e72d
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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