Methyl iodide → HCID 12567684, compound

Temperature

0 °C

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.

1. temperaturebefore being cooled to −78° C
2. temperatureto warm to room temperature
3. additionwas added dropwise
4. temperatureto warm to room temperature
5. extractionThe resulting mixture was extracted with ether
6. washwashed with saturated sodium bicarbonate and brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel chromatography
10. washeluting with 3:7 ethyl acetate

ORD record

ord-f366b8d5b8024639982bb5df24031e50

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402606B2