Methyl iodide → HCID 86623927, compound

HRID 898844Notes

Reaction equation

HRID 898844 reaction equation
[C:1]([O:5][C:6]([C@:8]1([C:19](=[O:24])[N:20]([O:22][CH3:23])[CH3:21])[C@@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:9]1[CH2:17][OH:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25]I>[Ag]=O>[C:1]([O:5][C:6]([C@:8]1([C:19](=[O:24])[N:20]([O:22][CH3:23])[CH3:21])[C@@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:9]1[CH2:17][O:18][CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 86623926HCID 86623926, compound

Product 1

HCID 86623927HCID 86623927, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst2×

Procedure

The above (1R*,2R*,3R*)-2-hydroxymethyl-1-(methoxy-methyl-carbamoyl)-3-phenyl-cyclopropanecarboxylic acid t-butyl ester (0.050 g, 0.15 mmol) was dissolved in 1 mL of methyl iodide. To this solution was added silver oxide (0.69 g, 3.0 mmol) and the mixture was stirred overnight at room temperature under N2 (in the dark). This reaction was incomplete and additional methyl iodide and silver oxide were added. After stirring overnight, the reaction appeared stalled. The catalyst was filtered off through celite and the residue was rinsed with ether. The filtrate was concentrated to a clear oil and purified by prep-TLC using 1:1 hexanes/EtOAc to afford 30 mg of the desired product (58%). This reaction was repeated numerous times to bring up more material. Note: If a huge excess of silver oxide was not used, the reaction often led to a reversion to the lactone product.

Workup

  1. stirringAfter stirring overnight
  2. filtrationThe catalyst was filtered off through celite
  3. washthe residue was rinsed with ether
  4. concentrationThe filtrate was concentrated to a clear oil
  5. custompurified

Sources & evidence

ORD record
ord-86878cfaf261419c82c1b7f16a2ab8d7
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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