反应详情

To a solution of 5-fluoro-3,3-dimethyl-1-nitroso-2,3-dihydro-1H-indole (4.03 g, 20.75 mmol) in THF (70 mL) at 0° C. is added a solution of LiAlH4 (40 mL, 40 mmol) in THF dropwise. The mixture is allowed to warm to rt and stirred overnight. The mixture is quenched with a saturated aqueous solution of Rochelle's Salt. The resulting mixture is stirred until a slurry is obtained. The organic phase is separated, washed with 10% aqueous HCl, saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 25% EtOAc in heptane to afford 5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-ylamine (3.51 g, 94%) as an oil. MS: 181 (M+H). 1H NMR (300 MHz, CD3Cl)): δ 6.85-6.78 (m, 1H), 6.75-6.68 (m, 2H), 3.44 (br s, 2H), 3.14 (s, 2H), 1.28 (s, 6H).

1. customThe mixture is quenched with a saturated aqueous solution of Rochelle's Salt
2. stirringThe resulting mixture is stirred until a slurry
3. customis obtained
4. customThe organic phase is separated
5. washwashed with 10% aqueous HCl, saturated aqueous NaHCO3, water and brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue is purified by silica gel chromatography
10. washeluting with 25% EtOAc in heptane