Triethylsilane → 3-[(4-Hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)-amino]-5-iodo-thiophene-2-carbox

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-iodo-3-[(4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (2.5 g, 4.96 mmol) and FeCl3 (41 mg, 0.252 mmol) in nitromethane (15.0 mL) cooled to 0° C. was added neat trimethyl-(tetrahydro-furan-3-yloxy)-silane (955 mg, 5.95 mmol) followed by the dropwise addition of triethylsilane (0.947 mL, 5.92 mmol). The reaction was allowed to slowly warm to room temperature and stirred overnight. Sat. NaHCO3 was added and the reaction mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a solid. The crude solid was heated in methanol, cooled and collected by filtration to provide 3-[(4-hydroxy-cyclohexyl)-(4-methyl-cyclohexanecarbonyl)-amino]-5-iodo-thiophene-2-carboxylic acid methyl ester (1.27 g, 44%) as a colorless solid.

Provenance & Evidence