反应 #586165

反应方程式

LiAlH4

THF

8

(4S)-3-[3-(5-methylindolyl)propanoyl]-4-phenyl-1,3-oxazolidin-2-one

THF

EtOAc

→

10

收率 92.0%

(2S)-2-[(5-methylindolyl)methyl]pent-4-en-1-ol

收率 92.0%

反应条件

后处理

1. 1
   温度raised to 0° C. (1 h)
2. 2
   workup.WAITAfter an additional 3 h at 0° C.
3. 3
   温度the reaction mixture was cooled to −78° C.
4. 4
   其他The reaction was quenched by the addition of ice-cold saturated NH4Cl solution (150 mL)
5. 5
   萃取extracted with Et2O
6. 6
   洗涤washed with brine
7. 7
   干燥dried (Na2SO4)
8. 8
   其他Evaporation
9. 9
   其他provided a residue, which
10. 10
    其他was purified by silica gel flash chromatography

实验过程

To a stirred suspension of LiAlH4 (718 mg, 17.90 mmol) in THF (60 mL) was added a precooled solution of 8 (5.78 g, 14.9 mmol) in THF (50 mL) at −78° C. under argon. The mixture was stirred at −78° C. (1 h), then raised to 0° C. (1 h). After an additional 3 h at 0° C., the reaction mixture was cooled to −78° C. and EtOAc (20 mL) was added followed by 10% NaOH (aq) (30 drops). The reaction was quenched by the addition of ice-cold saturated NH4Cl solution (150 mL), extracted with Et2O, washed with brine and dried (Na2SO4). Evaporation provided a residue, which was purified by silica gel flash chromatography to yielded 10 as colorless oil. (3.14 g, 92% yield). H NMR (d6-DMSO) δ 7.32-7.30 (m, 2H), 7.25 (d, 1H, J=2.9 Hz), 6.94 (dd, 1H, J=1.3 Hz & 8.5 Hz), 6.31 (dd, 1H, J=0.8 Hz & 3.1 Hz), 5.78 (m, 1H), 5.04-4.98 (m, 2H), 4.63 (t, 1H, J=5.0), 4.16 (dd, 1H, J=6.9 Hz & 14.2 Hz), 4.02 (dd, 1H, J=6.3 Hz & 14.2 Hz), 3.30-3.23 (m, 2H), 2.36 (s, 3H), 2.09-1.92 (m, 3H). FABMS (+Ve) m/z 229 [M+], 230 [MH+]. Anal. Calcd for C15H19NO C, 78.56; H, 8.35; N, 6.11. Found C, 78.47; H, 8.50; N, 6.16.

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