反应 #1178414

反应方程式

(S)-3-((benzyloxy)carbonyl)-2-(1,3-dioxoisoindolin-2-yl)propanoic acid

N-methylmorpholine

iso-butylchloroformate

compound 7-2

(S)-3-((benzyloxy)carbonyl)-2-(1,3-dioxoisoindolin-2-yl)propanoic acid

NaBH4

→

colorless oil

收率 92.2%

(S)-benzyl 4-hydroxy-3-(1,3-dioxoisoindolin-2-yl)butanoate

收率 92.2%

溶剂

THF

water

water

反应条件

后处理

1. 1
   其他at −15° C.
2. 2
   workup.STIRRINGThe reaction was stirred at −15° C. for 2 min
3. 3
   萃取Extracted with EtOAc (×3)
4. 4
   洗涤washed with water (×3), brine (×1)
5. 5
   干燥dried over sodium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated
8. 8
   其他Purification by chromatography on silica gel column (hexane/EtOAc)

实验过程

To a stirred solution of (S)-3-((benzyloxy)carbonyl)-2-(1,3-dioxoisoindolin-2-yl)propanoic acid (compound 7-2, 6.07 mmol) in 30 mL of dry THF at −15° C. were successively added N-methylmorpholine (6.07 mmol), iso-butylchloroformate (6.07 mmol). After stirring for 5 min at −15° C., a solution of NaBH4 (689 mg, 18.21 mmol) in 2.73 mL of water were added at once. The reaction was stirred at −15° C. for 2 min, then hydrolyzed with water (30 mL). Extracted with EtOAc (×3), washed with water (×3), brine (×1), dried over sodium sulfate, filtered, concentrated. Purification by chromatography on silica gel column (hexane/EtOAc) to give 1.9 g of colorless oil, compound 7-3.

来源