Reaktion #217100

Reaktionsgleichung

N-carbobenzoxy-3[(diethoxyphosphinyl)acetyl]piperidine-2-carboxylic acid

benzyl bromide

dicyclohexyl amine

→

title compound

Ausbeute 19.0%

N-Carbobenzoxy-3[(diethoxyphosphinyl)acetyl]piperidine-2-carboxylic acid benzyl ester

Ausbeute 19.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfilter
2. 2
   workup.ADDITIONPour the filtrate into water (11/2 L)
3. 3
   Extraktionextract with ethyl acetate (2×500 mL)
4. 4
   TrocknenCombine the organic phases and dry (MgSO4)
5. 5
   SonstigeEvaporate the solvent in vacuo
6. 6
   Sonstigeto give a brown oil
7. 7
   SonstigePurify by flash chromatography (ethyl acetate)

Vorschrift

Dissolve N-carbobenzoxy-3[(diethoxyphosphinyl)acetyl]piperidine-2-carboxylic acid (36.4 mmol) in dimethylformamide (200 mL) and place under a nitrogen atmosphere. Add benzyl bromide (10.5 mL), 81 mmol) and dicyclohexyl amine (16.2 mL, 89 mmol) and heat to 65° C. Allow to cool slowly to room temperature and filter. Pour the filtrate into water (11/2 L) and extract with ethyl acetate (2×500 mL). Combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo to give a brown oil. Purify by flash chromatography (ethyl acetate) to give the title compound as a yellow oil (3.6 g, 19%).

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