Reaktion #58040

Reaktionsgleichung

Water

Butyllithium

2-(diethoxy-phosphoryl)-succinic acid 4-benzyl ester 1-tert-butyl ester

trans-(4-Formyl-cyclohexyl)-carbamic acid tert-butyl ester

→

trans-2-(4-tert-Butoxycarbonylamino-cyclohexylmethylene)-succinic acid 4-benzyl ester 1-tert-butyl ester

Ausbeute 40.6%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was stirred at 0° C. for 1 h and at room temperature overnight
2. 2
   Extraktionthe product extracted with CH2Cl2
3. 3
   SonstigeThe organic phase was dried
4. 4
   Einengenconcentrated under reduced pressure

Vorschrift

Butyllithium (1.6 M in hexane, 5.0 ml, 8.00 mmol) was added dropwise to a solution of 2-(diethoxy-phosphoryl)-succinic acid 4-benzyl ester 1-tert-butyl ester (3.21 g, 8.00 mmol) in THF (25 mL) at 0° C. under nitrogen. After stirring at 0° C. for 1 h, the solution was transferred to a solution of trans-(4-Formyl-cyclohexyl)-carbamic acid tert-butyl ester (1.30 g, 5.72 mmol) in THF (10 mL). The resulting mixture was stirred at 0° C. for 1 h and at room temperature overnight. Water was added and the product extracted with CH2Cl2. The organic phase was dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 80:20) gave trans-2-(4-tert-Butoxycarbonylamino-cyclohexylmethylene)-succinic acid 4-benzyl ester 1-tert-butyl ester (1.10 g)

Quelle