反应详情

(R)-3-(N-Cyclobutylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (1.01 g, 4.02 mmol) was dissolved in anhydrous methanol (20 mL) and to this was n-propionaldehyde (3.0 mL, 40.2 mmol) added. After 1 h the reaction was cooled (ice-bath) then sodium cyanoborohydride (0.46 g, 7.24 mmol) was added, the pH was adjusted to 4-5 with acetic acid and the reaction was allowed to stir at room temperature over the weekend. The solvent was removed in vacuo, the remains were taken into a 2M solution of NH3 and then extracted thrice with diethyl ether. The combined ether portions were dried (MgSO4), filtered, and the solvent removed in vacuo to give the crude residue. Chromatography on silica (eluent 11% ethyl acetate/hexane) gave 0.95 g (80% yield) of the title compound as a clear oil. [α]21D =-95.4° (C=0.1; CHCl3). GC-MS (70 eV) M=293 (1%).

1. additionadded
2. temperatureAfter 1 h the reaction was cooled (ice-bath)
3. customThe solvent was removed in vacuo
4. extractionextracted thrice with diethyl ether
5. dry with materialThe combined ether portions were dried (MgSO4)
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customto give the crude residue