Reaktion #2279172

Reaktionsgleichung

H2O

1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate

2,3-dichloropyrazine

LiHMDS

→

1-tert-butyl 4-methyl 4-(3-chloropyrazin-2-yl)piperidine-1,4-dicarboxylate

Ausbeute 95.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc (3×20 mL)
2. 2
   WaschenThe combined organic layers were washed with saturated NaCl (10 mL)
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigePurification by ISCO (40 g SiO2, 0-75% EtOAc/Hexane)

Vorschrift

To a vial containing 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (408 mg, 1.678 mmol) and 2,3-dichloropyrazine (250 mg, 1.678 mmol) in THF (2.5 mL) at rt under N2 is added dropwise LiHMDS (1.678 mL, 1.678 mmol). The reaction was stirred at rt 16 h. The reaction mixture was poured into H2O (10 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with saturated NaCl (10 mL), dried (MgSO4), and concentrated. Purification by ISCO (40 g SiO2, 0-75% EtOAc/Hexane) gives 1-tert-butyl 4-methyl 4-(3-chloropyrazin-2-yl)piperidine-1,4-dicarboxylate (565 mg, 1.588 mmol, 95% yield) as a clear, colorless oil. [M+Na]=378.0

Quelle