反応 #51865

反応方程式

2-allylamino-1-(3-(S)-hydroxy-pyrrolidin-1-yl)-2-(S)-phenyl-ethanone

lithium aluminum hydride

→

title compound

収率 68.3%

1-(2-Allylamino-2-(S)-phenyl-ethyl)-pyrrolidin-3-(S)-ol

収率 68.3%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度to warm
2. 2
   温度The reaction was cooled to 0° C. in an ice bath
3. 3
   その他quenched with water (0.860 cm3), 15% sodium hydroxide (0.860 cm3) and water (2.60 cm3)
4. 4
   その他to form a white flocculate precipitate
5. 5
   ろ過filtered
6. 6
   洗浄the precipitate washed with tetrahydrofuran (5×30 cm3)
7. 7
   その他the filtrate volatile fractions removed in vacuo
8. 8
   その他to afford a crude yellow oil
9. 9
   その他The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol-ammonium hydroxide 97:3:0 to 90:10:1)

実験手順

To a stirred solution of 2-allylamino-1-(3-(S)-hydroxy-pyrrolidin-1-yl)-2-(S)-phenyl-ethanone (5.65 g, 15.1 mmol) in anhydrous tetrahydrofuran (60 cm3) cooled to 0° C. in an ice bath was added a 1 M solution of lithium aluminum hydride (22.6 cm3, 22.7 mmol) over 20 minutes. The solution was allowed to warm and stir at ambient temperature for 16 hours. The reaction was cooled to 0° C. in an ice bath and quenched with water (0.860 cm3), 15% sodium hydroxide (0.860 cm3) and water (2.60 cm3) to form a white flocculate precipitate. The mixture was vacuum filtered, the precipitate washed with tetrahydrofuran (5×30 cm3) and the filtrate volatile fractions removed in vacuo to afford a crude yellow oil. The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol-ammonium hydroxide 97:3:0 to 90:10:1) to afford the title compound as a yellow viscous oil (2.54 g, 68.3%) with a positive ion ESI (M+H)+247.2.

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