Reaktion #47631

Reaktionsgleichung

bicyclo[2.2.1]heptane-2-carbaldehyde

N-(benzyloxycarbonyl)-α-phosphonoglycine methyl ester

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

→

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

Ausbeute 36.2%

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
   workup.DISSOLUTIONdissolved in ethyl acetate (50 mL)
7. 7
   Waschenwashed with a saturated aqueous ammonium chloride solution (2×25 mL)
8. 8
   TrocknenThe organic layer was dried over sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated in vacuo
11. 11
    SonstigePurification by AnaLogix IntelliFlash chromatography (25 g column, 15% ethyl acetate/hexanes to 34% ethyl acetate/hexanes)

Vorschrift

In a round bottom flask was placed N-(benzyloxycarbonyl)-α-phosphonoglycine methyl ester (2.05 g, 6.18 mmol) in dichloromethane (5 mL) and cooled to 0° C. in an ice bath. To this mixture was then added slowly 1,8-diazabicyclo[5.4.0]undec-7-ene (801 μL, 5.36 mmol) and it was stirred at 0° C. for 20 min. The mixture was then treated with a solution of bicyclo[2.2.1]heptane-2-carbaldehyde (512 mg, 4.12 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 then dissolved 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, filtered and concentrated in vacuo. Purification by AnaLogix IntelliFlash chromatography (25 g column, 15% ethyl acetate/hexanes to 34% ethyl acetate/hexanes) afforded 2-benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-2-yl-acrylic acid methyl ester (491 mg, 36%) as a clear colorless oil.

Quelle