Methyl iodide → 1,8-Diethyl-1-(2-methoxyethyl)-1,3,4,9-tetrahydropyrano[3,4-b]indole

HRID 901056Notes

Reaction equation

HRID 901056 reaction equation
[CH2:1]([C:3]1([CH2:18][CH2:19][OH:20])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2].[H-].[Na+].[CH3:23]I>C1COCC1.[Cl-].[Na+].O>[CH2:1]([C:3]1([CH2:18][CH2:19][O:20][CH3:23])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 108910512-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

Product 1

HCID 160059801,8-Diethyl-1-(2-methoxyethyl)-1,3,4,9-tetrahydropyrano[3,4-b]indoleYield 62.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of compound 1 (348 mg, 1.27 mmol) in dry THF (5 mL) under argon, 60% NaH in mineral oil (64 mg, 1.59 mmol, 1.25 eq) was added in a portion-wise manner. After stirring for thirty minutes, MeI (99 μL, 1.59 mmol, 1.25 eq) was added dropwise, and the reaction was stirred for 2 days at room temperature. The resulting mixture was diluted with brine and extracted three times with Et2O. The combined organic phases were dried with Na2SO4, concentrated, and purified by column chromatography using 20:80:EtOAc:Hexane to give a yellow-white solid (228 mg, 62%): mp 125-126° C. 1HNMR (CDCl3, δ TMS): 0.86 (t, 3H), 1.37 (t, 3H), 1.94 (m, 2H), 2.15 (m, 2H), 2.78 (t, 2H), 2.85 (q, 2H), 3.37 (s, 3H), 3.52 (m, 2H), 4.00 (m, 2H), 6.99-7.38 (m, 3H, Ar—H), 8.43 (br, 1H, NH). MS−: m/z 286 ([M−H]−). Anal. (C18H25NO2): C, H, N.

Workup

  1. stirringthe reaction was stirred for 2 days at room temperature
  2. extractionextracted three times with Et2O
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-3dead50943f6400d9c340da1f1640767
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Reaction notes

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