Cerium(III) chloride → (3aS,4R,6aR)-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

Temperature

-78 °C

(3aR,6aR)-5-iodo-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (5-2) (1.5 g, 5.4 mmol, 1 equiv) was dissolved in MeOH (54 mL). The solution was cooled to −78° C. and cerium(III) chloride (1.4 g, 5.7 mmol, 1.05 equiv) was added followed by sodium borohydride (216 mg, 5.7 mmol, 1.05 equiv). The resulting mixture was stirred at the same temperature for 5 minutes. Upon disappearance of the starting material, the reaction was quenched with the addition of water (10 mL) and concentrated. The residue was partitioned between EtOAc (100 mL) and water (40 mL), the organics were dried over MgSO4, filtered and concentrated to afford (3aS,4R,6aR)-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (5-3) as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 6.31 (s, 1 II); 4.92 (dd, J=5.5, 2.0 Hz, 1H); 4.69 (t, J=5.5 Hz, 1H); 4.41 (dd, J=10.5, 5.5 Hz, 1H); 1.43 (s, 3H); 1.40 (s, 3H).

1. customUpon disappearance of the starting material, the reaction was quenched with the addition of water (10 mL)
2. concentrationconcentrated
3. customThe residue was partitioned between EtOAc (100 mL) and water (40 mL)
4. dry with materialthe organics were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-f94464b03c0942608cc0ffbed3fc63d6

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629275B2