Réaction #89766

Équation de réaction

(1S,2S)-2-(methoxycarbonyl)-4-oxocyclohexanecarboxylic acid

N,N-dimethylformamide

(benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

1-phenylpiperazine

N,N-diisopropylethylamine

→

product

Rendement 74.5%

methyl(1S,2S)-5-oxo-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexane-carboxylate

Rendement 74.5%

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was quenched with water (40 mL)
2. 2
   Extractionextracted with EtOAc (2×)
3. 3
   LavageThe combined organic layers were washed with brine
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutreThe residue was purified by Combiflash with 40-70% EtOAc/Hex

Mode opératoire

To a stirred solution of (1S,2S)-2-(methoxycarbonyl)-4-oxocyclohexanecarboxylic acid (1.014 g, 0.005065 mol) in anhydrous N,N-dimethylformamide (20.0 mL, 0.258 mol) at rt was added (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (2.989 g, 0.005572 mol), 1-phenylpiperazine (1.17 mL, 0.00760 mol), followed by N,N-diisopropylethylamine (2.66 mL, 0.0152 mol). The reaction mixture was stirred at rt for 15 h. The reaction was quenched with water (40 mL), extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by Combiflash with 40-70% EtOAc/Hex. to give the product as a colorless solid (1.299 g, 74% in yield). MS (ESI): (M+H)+=345.1.

Source