Reaktion #92582

Reaktionsgleichung

di-tert-butyl azodicarboxylate

ethyl 1-benzylpiperidine-4-carboxylate

diisopropylamine

n-BuLi

→

crude product

Ausbeute 73.3%

di-tert-Butyl 1-(1-benzyl-4-(ethoxycarbonyl)piperidin-4-yl)hydrazine-1,2-dicarboxylate

Ausbeute 73.3%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred for 30 min
2. 2
   Sonstigequenched with aqueous NH4Cl (10 mL)
3. 3
   Extraktionextracted with EA (10 mL×3)
4. 4
   TrocknenThe combined organic layers were dried over Na2SO4
5. 5
   Einengenconcentrated

Vorschrift

To a solution of diisopropylamine (153 mg, 1.5 mmol) in THF (20 mL) was added n-BuLi (2.5 M, 0.6 mL) at −75° C. under N2. After 5 min, ethyl 1-benzylpiperidine-4-carboxylate (247 mg, 1.0 mmol) was added and the resulting mixture then stirred at −70° C. for 10 min, before adding di-tert-butyl azodicarboxylate (345 mg, 1.5 mmol). The reaction was stirred for 30 min, then quenched with aqueous NH4Cl (10 mL) and extracted with EA (10 mL×3). The combined organic layers were dried over Na2SO4 and concentrated to give the crude product (350 mg, 72%) as an off-white solid. MS (ESI, m/e) [M+1]+ 478.3.

Quelle