Imidazole → (1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-t-butyldimethylsilyloxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate

HRID 2271286

Reaktionsgleichung

Reaktionsgleichung von HRID 2271286
[F:1][C:2]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]2[CH:3]1[CH:4]([OH:9])[CH2:5][C:6]2=[O:8].[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].CN(C)C=O.N1C=CN=C1>O>[F:1][C:2]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:3]2[CH:7]1[CH:6]([O:8][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21])[CH2:5][C:4]2=[O:9]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 69853523(1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-hydroxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate

Produkt 1

HCID 70184270(1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-t-butyldimethylsilyloxy-2-oxobicyclo[3.1.0]hexane-6-carboxylateAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2.8 g of (1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-hydroxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate and 2.5 g of t-butyldimethylchlorosilane were dissolved into 14 ml of N,N-dimethylformamide. 1.0 g of imidazole was further added thereto with ice-cooling, and this was stirred at room temperature for one day. The reaction solution was poured into water, and extracted with n-hexane-ethyl acetate (1:9). The obtained organic layer was washed with, in sequence, water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. After filtering off the desiccant, concentration of the filtrate was carried out under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=15:1), yielding 3.8 g of (1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-t-butyldimethylsilyloxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate. The proton NMR and mass spectrograph data are shown below.

Aufarbeitung

  1. temperaturewith ice-cooling
  2. extractionextracted with n-hexane-ethyl acetate (1:9)
  3. washThe obtained organic layer was washed with, in sequence, water
  4. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  5. filtrationAfter filtering off the desiccant, concentration of the filtrate
  6. customThe residue was purified by column chromatography (silica gel: Wako gel (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-a84c11ef540746c0baf4c5edf220658f
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06333428B1

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