反应详情

The product of Example 61B (60.0 g, 0.159 mol) in tetrahydrofuran (200 mL) was added dropwise to a mixture of lithium aluminum hydride (7.00 g, 0.175 mol, 95%) in tetrahydrofuran (300 mL) at 0° C. After the addition was complete, the mixture was allowed to warm to ambient temperature and was quenched by slow addition of Na2SO4.10H2O (excess). The mixture was stirred for 16 hours, filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 50% ethyl acetate/hexanes) to provide two diastereomers, a more mobile diastereomer determined to be the (3S,4S) diastereomer Rf=0.27 in 75% ethyl acetate/hexanes, 15.0 g, 44.8 mmol, 28% yield and a less mobile diastereomer determined to be the (3R,4R) diastereomer (Rf=0.20 in 75% ethyl acetate/hexanes, 22.5 g, 67.3 mmol, 42% yield). MS (DCI/NH3) m/z 335 (M+H)+.

1. additionAfter the addition
2. customwas quenched by slow addition of Na2SO4.10H2O (excess)
3. filtrationfiltered
4. concentrationthe filtrate concentrated under reduced pressure
5. customThe residue was purified by column chromatography (SiO2, 50% ethyl acetate/hexanes)
6. customto provide two diastereomers