Reaktion #87119

Reaktionsgleichung

(S)-tert-butyl (3-cyclopentyl-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate

vinylmagnesium bromide

→

(S)-tert-butyl (1-cyclopentyl-3-oxopent-4-en-2-yl)carbamate

Ausbeute 38.5%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   Sonstigequenched with saturated aqueous ammonium chloride (30 mL)
3. 3
   ExtraktionThe resulting mixture was extracted with EtOAc (2×40 mL)
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=100:1)

Vorschrift

To a solution of (S)-tert-butyl (3-cyclopentyl-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (2.5 g, 8.3 mmol) in THF (35 mL) was added vinylmagnesium bromide (16.7 mL, 33.3 mol) at 0° C. dropwise. After completion of the addition, the reaction mixture was stirred at 0° C. for 2 h and then quenched with saturated aqueous ammonium chloride (30 mL). The resulting mixture was extracted with EtOAc (2×40 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=100:1) to afford (S)-tert-butyl (1-cyclopentyl-3-oxopent-4-en-2-yl)carbamate as a yellow oil (854 mg, 38% yield).

Quelle