Sodium Methoxide → (+)-(1R,2S,5R)-5-(hydroxymethyl)cyclopent-3-ene-1,2-diol

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Reaction Steps

To a stirred solution of (1R,2S,5R)-5-(hydroxymethyl)cyclopent-3-ene-1,2-diyl dibenzoate (9) (19.2 g, 56.7 mmol) in methanol at room temperature under nitrogen atmosphere sodium methoxide (25 wt % in methanol) (38.9 mL, 170 mmol) was added drop wise over a period of 20 minutes. The mixture was stirred at room temperature for 2 h and quenched by drop wise addition of 1N HCl solution to neutral pH. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (5% Methanol/DCM) to give triol 10 (6.1 g, 84%) as an oil; [α]24D +254.04° (c 1.0, MeOH); 1H NMR (500 MHz, CD3OD) δ 2.78 (d, J=5.0 Hz, 1H), 3.73 (dd, J=5.0, 11.0 Hz, 1H), 3.55 (dd, J=6.5, 10.5 Hz, 1H), 3.93 (t, 1H), 4.50 (t, 1H), 5.88-5.87 (m, 1H), 5.97 (d, J=6.0 Hz, 1H); 13C NMR (125 MHz, CD3OD) δ 53.7, 62.2, 73.2, 74.5, 132.0, 135.0; HR-MS Calcd. For (C6H10O3—H)+ 129.0630. found 129.0553.

Provenance & Evidence