[(3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate → [(3aR,4R,6R,6aS)-6-(6-isobutyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of [(3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate (250.0 mg, 0.68 mmol) in degassed THF (6 mL) under nitrogen was added Pd(PPh3)4 (44 mg, 0.038 mmol) followed by 0.5 M of isobutylzinc bromide in tetrahydrofuran (2.04 mL) dropwise over 15 min. The reaction was heated at 60° C. for 1 hour. The reaction was cooled then quenched with saturated aq NH4Cl, extracted with EtOAc and the organic phase was washed with saturated aq EDTA.Na2 solution then water. The organic phase was concentrated and the residue purified by flash chromatography (0 to 100% EtOAc/DCM) to provide the title compound (120 mg, 45%).

Provenance & Evidence