Hydrogen Peroxide → HCID 67951398, compound

Participants

Reaction Steps

Borane-THF complex in tetrahydrofuran (1M, 0.99 mL, 0.99 mmol) was added to a 0° C. solution of benzyl((3aS,4R,6aR)-2,2-dimethyl-6-methylenetetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate (0.150 g, 0.494 mmol) in tetrahydrofuran (10 mL, 0.1 mol). Some bubbling initially observed, the mixture stirred at room temperature for 1 hour. The reaction was quenched via the addition of aqueous sodium hydroxide (4M, 1.24 mL, 0.00494 mol) and hydrogen peroxide 35% (35%, 0.425 ml, 4.94 mmol) were added and reaction stirred at room temperature for 2.5 hours. Water (5 ml) added to the reaction and the aqueous was extracted with ether (3×50 mls). The combined organics were dried with MgSO4 and purified by FC (Hex/EtOAc 1:1) to yield benzyl((3aS,4R,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate (0.070 g, 44%) as a thick colorless oil: MS (ESI+) for C17H23NO5 m/z 344.2 [M+Na]+; MS (ESI−) for C17H23NO5 m/z 320.3 [M−H]−;

Provenance & Evidence