Reaktion #47640

Reaktionsgleichung

bicyclo[2.2.1]heptane-7-carbaldehyde

N-(benzyloxycarbonyl)-α-phosphonoglycine methyl ester

1,8-diazabicyclo[5.4.0]undec-7-ene

→

2-benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-7-yl-acrylic acid methyl ester

Ausbeute 33.5%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a round bottom flask was placed
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Temperaturto warm to 25° C.
4. 4
   workup.STIRRINGstirred overnight
5. 5
   EinengenThe mixture was concentrated in vacuo
6. 6
   Waschenwashed with a saturated aqueous ammonium chloride solution (2×25 mL)
7. 7
   TrocknenThe organic layer was dried over sodium sulfate
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigePurification by AnaLogix IntelliFlash flash chromatography (4 g column, 5% ethyl acetate/hexanes to 20% ethyl acetate/hexanes)

Vorschrift

In a round bottom flask was placed N-(benzyloxycarbonyl)-α-phosphonoglycine methyl ester (680 mg, 2.05 mmol) in dichloromethane (5 mL) and cooled to 0° C. in an ice bath. To this mixture was added slowly 1,8-diazabicyclo[5.4.0]undec-7-ene (266 μL, 1.78 mmol) and stirred at 0° C. for 20 min. The mixture was treated with a solution of bicyclo[2.2.1]heptane-7-carbaldehyde (170 mg, 1.36 mmol) in dichloromethane (5 mL). After the addition was complete, the mixture was allowed to warm to 25° C. and stirred overnight. The mixture was concentrated in vacuo and the residue taken up in ethyl acetate (50 mL) and washed with a saturated aqueous ammonium chloride solution (2×25 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification by AnaLogix IntelliFlash flash chromatography (4 g column, 5% ethyl acetate/hexanes to 20% ethyl acetate/hexanes) afforded 2-benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-7-yl-acrylic acid methyl ester (150 mg, 33%) as a clear colorless oil.

Quelle