反応 #1838901

反応方程式

(2S,5R)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidine-2-carboxylic acid

lithium borohydride

→

crude product

収率 88.8%

(2S,5R)-1-(tert-butoxycarbonyl)-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid

収率 88.8%

溶媒

diethyl ether

methanol

反応条件

後処理

1. 1
   その他the ice bath was removed
2. 2
   温度the reaction was heated
3. 3
   温度at reflux overnight
4. 4
   温度The reaction mixture was cooled to 0° C.
5. 5
   その他quenched with 1N HCl
6. 6
   抽出extracted into ethyl acetate
7. 7
   乾燥dried over sodium sulphate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated under reduced pressure

実験手順

To an ice cold solution of (2S,5R)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidine-2-carboxylic acid (1.17 g, 4.07 mmol) in 70 mL diethyl ether and 0.330 mL methanol was added lithium borohydride (2M in THF, 4.0 mL, 8.14 mmol). After 10 minutes, the ice bath was removed and the reaction was heated at reflux overnight. As the reaction had not proceeded, a solvent swap to THF was performed, and the resulting mixture was heated at 70° C. overnight. The reaction mixture was cooled to 0° C. and quenched with 1N HCl and then extracted into ethyl acetate, dried over sodium sulphate, filtered and concentrated under reduced pressure to give the crude product as a white semi-solid (886 mg)

出典