反应详情

Glacial acetic acid (25 mL) in a 250 mL 3-neck flask was cooled in an ice bath under a stream of nitrogen. Sodium borohydride was added cautiously in portions over a 5 minute period. The ice bath removed and the reagent was used after stirring for 15 minutes at ambient temperature. 2-Benzoyloxy-4-hydroxymethylcyclobutanone (1.43 g, 6.5 mmol) from Step H was dissolved in 45 mL of glacial actetic acid and immediately treated with the above borohydride reagent. After stirring the reaction mixture for 35 minutes, the reaction was quenched with ~2 mL of methanol and the reaction mixture was concentrated in vacuo to a syrup. The syrup was dissolved in 250 mL of ethyl acetate and the ethyl acetate solution was washed with water and 5% aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to give 1.47 g of the title compound which was taken on to the next step without purification; MS DCI-NH3M/Z: 221 (M+H)+, 238 (M+NH4)+.

1. customThe ice bath removed
2. stirringAfter stirring the reaction mixture for 35 minutes
3. customthe reaction was quenched with ~2 mL of methanol
4. concentrationthe reaction mixture was concentrated in vacuo to a syrup
5. dissolutionThe syrup was dissolved in 250 mL of ethyl acetate
6. washthe ethyl acetate solution was washed with water and 5% aqueous sodium bicarbonate
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated