Reaktion #60584

Reaktionsgleichung

ammonium chloride

aniline

n-butyl lithium

1-t-butoxycarbonyl-3-piperidinecarboxylic acid

sodium hydride

oxalyl chloride

→

1-t-butoxycarbonylpiperidine-3-carboxanilide

Ausbeute 71.8%

Lösungsmittel

tetrahydrofuran

dichloromethane

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction mixture at 0° C
2. 2
   workup.WAITAfter additional 30 min
3. 3
   Sonstigethe whole reaction mixture
4. 4
   Extraktionwas extracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Sonstigeevaporated in vacuo
8. 8
   SonstigePurification of the residue by silica gel column chromatography (hexane-ethyl acetate)

Vorschrift

A solution of 1-t-butoxycarbonyl-3-piperidinecarboxylic acid (458 mg, 2.00 mmol), sodium hydride (88 mg, 2.20 mmol, 60% oil suspension), oxalyl chloride (0.22 ml, 2.50 mmol) and catalytic amount of dimethylformamide (0.20 ml) in dichloromethane (16 ml) was stirred at 0° C. After stirring for 30 min, aniline (0.20 ml, 2.20 mmol) which was treated with n-butyl lithium (1.45 ml, 2.30 mmol, 1.59 M in hexane) in tetrahydrofuran (4 ml) was added to the reaction mixture at 0° C. After additional 30 min, saturated ammonium chloride was added and the whole reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo. Purification of the residue by silica gel column chromatography (hexane-ethyl acetate) gave 1-t-butoxycarbonylpiperidine-3-carboxanilide (437 mg, 71%).

Quelle