Реакция #1178414

Уравнение реакции

(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

Выход 92.2%

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

Выход 92.2%

Растворители

THF

water

water

Условия реакции

Обработка

1. 1
   Другоеat −15° C.
2. 2
   workup.STIRRINGThe reaction was stirred at −15° C. for 2 min
3. 3
   ЭкстракцияExtracted with EtOAc (×3)
4. 4
   Промывкаwashed with water (×3), brine (×1)
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   ДругоеPurification by chromatography on silica gel column (hexane/EtOAc)

Методика

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.

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