Methyl iodide → HCID 12567684, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 9.09 mL (65 mmol) of diisopropylamine in 100 mL of tetrahydrofuran was added dropwise 40.5 mL (65 mmol) of 1.6 M n-butyl lithium in hexanes. The solution was allowed to warm to 0° C. briefly before being cooled to −78° C. To the solution was added 4.09 mL (30.9 mmol) of dimethyl (S)-(−)-malate dropwise and the resulting solution was allowed to warm to room temperature. After 30 min at room temperature, it was cooled to −78° C. before 2.3 mL (37.1 mmol) of methyl iodide was added dropwise. The solution was allowed to warm to room temperature, and was stirred for 18 h. It was then poured onto a mixture of ether, ice water, and 9.27 mL of acetic acid. The resulting mixture was extracted with ether, and the extracts were combined, washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 3:7 ethyl acetate:hexanes to afford 1.04 g (5.9 mmol) of dimethyl (2S,3S)-2-hydroxy-3-methylbutanedioate.

Provenance & Evidence