Reaktion #1178414

Reaktionsgleichung

(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

Ausbeute 92.2%

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

Ausbeute 92.2%

Lösungsmittel

THF

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat −15° C.
2. 2
   workup.STIRRINGThe reaction was stirred at −15° C. for 2 min
3. 3
   ExtraktionExtracted with EtOAc (×3)
4. 4
   Waschenwashed with water (×3), brine (×1)
5. 5
   Trocknendried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigePurification by chromatography on silica gel column (hexane/EtOAc)

Vorschrift

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.

Quelle