Methyl iodide → HCID 178429783, compound

Participants

Reaction Steps

A solution of 1-(trans-4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-1H-pyrazole (2.00 g, 4.92 mmol) in THF (20 mL, 200 mmol) was cooled to −78° C., and 1.5 M of Lithium Diisopropylamide in Cyclohexane (4.26 mL, 6.40 mmol) was added. After stirring for 5 min, Methyl iodide (2 mL, 20 mmol) was added slowly, and the mixture was stirred at −78° C. for 30 min. Sat. NH4Cl was added to quench, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was dry-loaded onto silica gel for column chromatography, eluting with 1% EtOAc/heptane. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. 1H NMR (400 MHz, methanol-d4): δ=0.11 (s, 6H), 0.93 (s, 9H), 1.48-1.60 (m, 2H), 1.85-2.05 (m, 6H), 2.34 (s, 3H), 3.70-3.81 (m, 1H), 4.16-4.26 (m, 1H), 7.43 (s, 1H).

Provenance & Evidence