Methyl iodide → HCID 86705495, compound

Participants

Reaction Steps

To a solution of 174 (2.22 g, 6.93 mmol) and THF (30 mL).cooled to 0° C. and maintained under a N2 atmosphere was added NaH (0.333 g, 8.32 mmol, 60% in mineral oil). The ice bath was removed and the solution stirred for 30 min then MeI (0.519 mL, 8.32 mmol) was added and the yellow solution stirred overnight. The reaction was diluted with H2O and extracted with Et2O. The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography (SNAP 50) eluting with hexane/EtOAc (4:1) to afford 0.660 g (28%) of (R)-tert-butyl 1-(3,4-dichlorophenyl)-3-methoxypropylcarbamate (176) as a light yellow oil.

Provenance & Evidence