Isopropanol → 2-(3-(Benzyloxycarbonyl)-1-hydroxycyclopentyl)acetic acid

Participants

Reaction Steps

To a solution of benzyl 3-allyl-3-hydroxycyclopentanecarboxylate (from step A, 150 mg, 0.576 mmol) in ethyl acetate (5 mL) was added ruthenium (IV) oxide hydrate (104 mg, 0.691 mmol) followed by 10% wt. aqueous sodium periodate solution (˜3 mL). The resulting mixture was stirred at room temperature for 4 hours. Isopropyl alcohol (3 mL) was added to quench the reaction. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to yield 2-(3-(benzyloxycarbonyl)-1-hydroxycyclopentyl)acetic acid (130 mg, 0.467 mmol, 81% yield) as an oil. It was used as such for the next step without further purification. MS (ESI+) m/z 301 (M+Na)+

Provenance & Evidence