Reaktion #87124

Reaktionsgleichung

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

prop-1-en-2-ylmagnesium bromide

→

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

Ausbeute 52.1%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   Sonstigethen quenched with saturated aqueous ammonium chloride (500 mL)
3. 3
   ExtraktionThe resulting mixture was extracted with EtOAc (400 mL×2)
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-(cyclopent-1-en-1-yl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (81 g, 0.27 mol) in THF (600 mL) was added freshly prepared prop-1-en-2-ylmagnesium bromide (96.0 mL, 1.08 mol) at 0° C. dropwise. After completion of the addition, the reaction mixture was stirred at 0° C. for 2 h then quenched with saturated aqueous ammonium chloride (500 mL). The resulting mixture was extracted with EtOAc (400 mL×2). The organic phases 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-(cyclopent-1-en-1-yl)-4-methyl-3-oxopent-4-en-2-yl)carbamate as colorless oil (39.3 g, 52% yield).

Quelle