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

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.

1. customquenched by drop wise addition of 1N HCl solution to neutral pH
2. customThe solvent was removed under reduced pressure
3. customthe residue was purified by silica gel column chromatography (5% Methanol/DCM)

ORD record

ord-086003b766714dfc903023ced93e203e

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334273B1