反应详情

To a solution of 200 mg of methyl 1-(p-chlorobenzyl)-3-(t-butylthio)-α,α-dimethyl-5-(i-propyl)-indole-2-propanoate (from Example 25) in 1.5 mL tetrahydrofuran (THF) was added 0.4 ml of a solution of lithium aluminum hydride (1.0 M in THF) at 0° C. After 2h at 0° C., the reaction mixture was quenched with saturated aqueous Na2SO4, diluted with ether and stirred at room temperature for 1 h. The resultant slurry was filtered and the filtrate concentrated to dryness. The resultant oil was purified by flash chromatography (eluant: hexane-ethyl acetate, 8:2) to give the title compound as a viscous oil. 1H NMR (250 MHz, Acetone D ) δ: 0.94 (s, 9H), 1.26 (s, 6H), 1.27 (d, 2H J=7.0 Hz), 2.95-3.08 (m, 2H), 2.99 (septuplet, 1H, J=7.0 Hz), 3.27 (d, 2H, J=7.0 Hz), 4.02 (t, 1H, J=7.0 Hz, exchanges with D20), 4.69 (broad s, 2H), 6.92 (d, 2H, J=8.5 Hz), 7.00 (dd, 1H, J=7.5 and 2.0 Hz), 7.24 (d, 1H, J=7.5 Hz); 7.29 (d, 2H, J=8.5 Hz), 7.58 (d, 1H, J=2.0 Hz) IR (CDCl3) 3420 cm-1.

1. customAfter 2h at 0° C., the reaction mixture was quenched with saturated aqueous Na2SO4
2. additiondiluted with ether
3. filtrationThe resultant slurry was filtered
4. concentrationthe filtrate concentrated to dryness
5. customThe resultant oil was purified by flash chromatography (eluant: hexane-ethyl acetate, 8:2)