反应详情

A 4 N hydrochloric acid/ethyl acetate solution (40 mL) of {(1R,2R)-2-benzyloxy-1-[2-(4-chlorophenyl)-2-oxoethoxymethyl]propyl}carbamic acid t-butyl ester (2.61 g) was stirred for 1 hour at room temperature. The solvent was removed under a vacuum, and methanol (30 mL) was added. Under ice-cooling, sodium cyanoborohydride (733 mg) was added, and the resultant was stirred overnight at room temperature. The solvent was removed under a vacuum, and the resultant was diluted with ethyl acetate and washed with saturated sodium bicarbonate aqueous solution and brine in sequence, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the residue was purified with silica gel column chromatography (heptane/ethyl acetate 95/5→3/2), and the title compound (1.435 g) was obtained. The physical property values are as follows.

1. customThe solvent was removed under a vacuum, and methanol (30 mL)
2. additionwas added
3. temperatureUnder ice-cooling
4. additionsodium cyanoborohydride (733 mg) was added
5. customThe solvent was removed under a vacuum
6. additionthe resultant was diluted with ethyl acetate
7. washwashed with saturated sodium bicarbonate aqueous solution and brine in sequence
8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
9. customThe solvent was removed under a vacuum
10. customthe residue was purified with silica gel column chromatography (heptane/ethyl acetate 95/5→3/2)