反应详情

温度

-78 °C

To a stirred solution of 4-(9H-fluoren-9-ylmethyl) 3-methyl 3,4-morpholinedicarboxylate (0.6 g, 1.633 mmol) in anhydrous toluene (80 mL) cooled to −78° C. in a dry-ice acetone bath under nitrogen was added dropwise 1.0 M diisobutylaluminium hydride in hexanes (6.53 mL, 6.53 mmol) over 4 minutes. The solution was stirred at −78° C. for 1.5 hours. The reaction was quenched at −78° C. with methanol (1.5 mL) and then aqueous HCl (1 M, 50 mL). The mixture was allowed to warm to ambient temperature and the phases separated. The aqueous was washed with ethyl acetate (2×50 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to leave an oil. The residue was loaded in dichloromethane and purified by flash chromatography (Si) using 0-100% ethyl acetate-cyclohexane over 30 minutes. The appropriate fractions were combined and evaporated in vacuo to give the required product as a white foam, 329 mg. LCMS [LCMS4] Rt 2.43 min, m/z (ES+) 338 (M+H).

1. customThe reaction was quenched at −78° C. with methanol (1.5 mL)
2. temperatureto warm to ambient temperature
3. customthe phases separated
4. washThe aqueous was washed with ethyl acetate (2×50 mL)
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customto leave an oil
9. custompurified by flash chromatography (Si)
10. customover 30 minutes
11. customevaporated in vacuo