General procedure for the synthesis of cis-3-(benzyloxy)cyclobutanol from 3-(benzyloxy)-1-cyclobutanone: To a solution of 3-(benzyloxy)cyclobutan-1-one (300 mg, 1.71 mmol) in anhydrous ethanol (5 mL) was added sodium borohydride (65 mg, 1.71 mmol) in batches at 0 °C. The reaction mixture was stirred continuously at this temperature for 3 hours. Upon completion of the reaction, the reaction was quenched by the addition of ice water and extracted with ethyl acetate (EtOAc). The organic layers were combined, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography with hexane solution of 10% ethyl acetate as eluent to give cis-3-(benzyloxy)cyclobutanol as a light yellow oil (300 mg, 99% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 1.69-1.76 (m, 2H), 2.49-2.55 (m, 2H), 3.49-3.72 (m, 2H), 4.33 (s, 2H), 4.97-5.01 (m, 1H), 7.25-7.35 (m, 5H).
