HCID 54201797, compound → HCID 58081142, compound

Participants

Reaction Steps

Methylmagnesium bromide (1.4 M solution in toluene/THF) (3.667 ml, 5.134 mmol) was added dropwise to a cooled solution (at 0° C.) of intermediate D30 (0.5 g, 1.711 mmol) in THF (20 ml) under a N2 atmosphere. The resulting reaction mixture was warmed to room temperature and further stirred for 4 h. After cooling in an ice bath, the mixture was carefully quenched with NH4Cl (aqueous sat. solution), and was subsequently extracted with DCM. The organic layer was separated, dried (Na2SO4), and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-30% EtOAc/heptane as eluent). The desired fractions were collected and the solvent was evaporated in vacuo to yield cis-D33 (0.096 g, 18.2%) and trans-D33 (0.12 g, 22.7%).

Provenance & Evidence