Trimethylsilyldiazomethane → HCID 66631998, compound

Participants

Reaction Steps

To a solution of (S)-2-(5-bromo-2-(hydroxymethyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetic acid (3.6 g, 9.4 mmol) in anhydrous dichloromethane and methanol (1:1, 20 mL) was added (trimethylsilyl)diazomethane (2 M in hexanes, 5.17 mL, 10.34 mmol) and the reaction was stirred at room temperature for three hours. An additional 2 mL of (trimethylsilyl)diazomethane was added and stirred for 2 hours, followed by an additional 1 mL of (trimethylsilyl)diazomethane for 1 hour, then 1 mL of (trimethylsilyl)diazomethane added and let go overnight. An additional 3.5 mL of (trimethylsilyl)diazomethane were added and stirred for 1 hour. The reaction was quenched with 30 mL of acetic acid and then stirred 15 minutes. The reaction was concentrated under reduced pressure and then absorbed onto silica. The crude reaction was purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a yellow foam (2.37 g). LCMS-ESI+ (m/z): [M+H]+ calcd C18H23BrNO4: 396.07. found: 396.71.

Provenance & Evidence