Potassium Carbonate → HCID 25130206, compound

Participants

Reaction Conditions

Reaction Steps

A solution composed of {(7R,8R)-7-[(benzyloxy)methyl]-1,4-dioxaspiro[4.5]dec-8-yl}methanol (33.6 g, 115 mmol) in a mixture of acetic acid (220 mL) and water (80 mL) was heated at 85° C. for 2 h. The solvents were removed by rotary evaporation under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted with an additional portion of ethyl acetate and the combined organics were washed with saturated aqueous NaHCO3 and NaCl solutions, and dried over a mixture of Na2SO4 and MgSO4. Concentration in vacuo afforded a yellow syrup that was taken up in methanol (250 mL) and treated with K2CO3 (20 g, 150 mmol) with stirring at rt for 30 min. The methanol was then evaporated and the residue was taken up in ethyl acetate and washed with water, saturated aqueous NaCl solution, and dried a mixture of Na2SO4 and MgSO4. Concentration in vacuo provided (3R,4R)-3-[(benzyloxy)methyl]-4-(hydroxymethyl)cyclohexanone as a thick, yellow syrup. 1H NMR (500 MHz, d6-acetone) δ 7.36 (4H, m), 7.30 (1H, m), 4.56-4.50 (2H, m), 3.70 (1H, m), 3.66-3.60 (2H, m), 3.56 (1H, dd, J= 5.4, 9.3 Hz), 3.54-3.48 (1H, dd, J= 4.0, 9.3 Hz), 2.44-2.26 (4H, m), 2.13-2.07 (2H, m), 1.91 (1H, m), 1.67 (1H, m).

Provenance & Evidence