Methyl iodide → HCID 57899233, compound

HRID 1802775Notes

Reaction equation

HRID 1802775 reaction equation
[CH3:1][O:2][C:3](=[O:24])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[NH:23][N:22]=[N:21][N:20]=2)=[CH:8][CH:7]=1.I[CH3:26].[OH-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:24])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[N:23]=[N:22][N:21]([CH3:26])[N:20]=2)=[CH:10][CH:11]=1.[CH3:1][O:2][C:3](=[O:24])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[N:20]([CH3:26])[N:21]=[N:22][N:23]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178499754HCID 178499754, compound

Product 2

HCID 57899233HCID 57899233, compoundYield 27%HCID 57899291HCID 57899291, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-(4-{1-[2-(1H-tetrazol-5-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (1.0 g, 2.1 mmol) in dimethylformamide (5 mL) was added iodomethane (1.91 mL, 30.6 mmol) and sodium hydroxide (1.64 g, 30.7 mmol). The reaction was stirred at room temperature for 2 h, ice water was added, and the resulting mixture was extracted several times with ethyl acetate. The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel column chromatography to give (E)-3-(4-{1-[2-(2-methyl-2H-tetrazol-5-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (0.15 g, 21%, LCMS (m/z): 342.1 (M+1)) and (E)-3-(4-{1-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (0.20 g, 27%, LCMS (m/z): 342.1 (M+1)).

Workup

  1. extractionthe resulting mixture was extracted several times with ethyl acetate
  2. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-403b50c4101243cca2829c868b55c30e
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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