Iodine → (3aR,6aR)-5-iodo-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

3aR,6aR)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (5-1) (1.2 g, 7.8 mmol, 1 equiv) was dissolved in DCM (50 mL) and pyridine (0.9 mL, 10.9 mmol, 1.4 equiv) was added followed by a solution of iodine (3.4 g, 13.2 mmol, 1.7 equiv) in THF (6 mL). The resulting mixture stirred overnight at ambient temperature. Upon disappearance of starting material, the reaction mixture was poured over water (30 mL), extracted with CHCl3 (3×50 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (80 g SiO2, 0-40% EtOAc in hexanes) to yield (3aR,6aR)-5-iodo-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (5-2) as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 7.97 (d, J=2.5 Hz, 1H); 5.22 (dd, J=5.5, 2.5 Hz, 1H); 4.53 (d, J=5.5 Hz, 1H); 1.42 (s, 3H); 1.39 (s, 3H).

1. extractionextracted with CHCl3 (3×50 mL)
2. dry with materialdried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customThe crude residue was purified by flash chromatography (80 g SiO2, 0-40% EtOAc in hexanes)

ORD record

ord-35540e3064fd404eae55ba65e82ba561

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629275B2