Reaktion #714254

Reaktionsgleichung

(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Intermediate 5

(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

prop-1-en-2-ylmagnesium bromide

→

desired product

Ausbeute 89.3%

(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamate

Ausbeute 89.3%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with 200 mL 10% citric acid
2. 2
   workup.ADDITIONdiluted further with 100 mL water
3. 3
   Extraktionextracted with ether
4. 4
   EinengenThe organics were concentrated
5. 5
   workup.DISSOLUTIONthe resulting oil was dissolved in ether
6. 6
   Waschenwashed with water and brine
7. 7
   TrocknenThe organics were dried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated

Vorschrift

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (Intermediate 5, 30.79 g, 76.48 mmol) in THF (200 mL) at 0° C. was added prop-1-en-2-ylmagnesium bromide (0.5M in THF) (300 mL, 149.90 mmol). The reaction mixture was stirred at 0° C. for 1 hour. The reaction mixture was quenched with 200 mL 10% citric acid, diluted further with 100 mL water and extracted with ether. The organics were concentrated and the resulting oil was dissolved in ether and washed with water and brine. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the desired product (26.2 g, 89%) as a colorless oil.

Quelle