Reaktion #725283

Reaktionsgleichung

3D

benzyl 2,4-dibromo-3-methylbutyrate

aminodiphenylmethane

→

N-diphenylmethyl-cis-3-methyl-2-azetidinecarboxylic acid benzyl ester

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 40 hours
2. 2
   TemperaturThe mixture was cooled
3. 3
   Filtrationfiltered
4. 4
   Einengenthe filtrate was concentrated to dryness under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in the minimum amount of methylene chloride
6. 6
   Filtrationthe solution was filtered through a short column of silica gel
7. 7
   workup.ADDITIONv mixture of hexane and ether as eluent
8. 8
   SonstigeThe solvents were evaporated
9. 9
   workup.ADDITIONv mixture of hexane and ether as eluent
10. 10
    SonstigeThe less polar portions thus obtained
11. 11
    Sonstigethe solvents were evaporated
12. 12
    Sonstigethe residue crystallized from methylene chloride/hexane

Vorschrift

A stirred mixture of 23.94 g of 3D, 37.6 g of aminodiphenylmethane and 170 ml of acetonitrile was refluxed for 40 hours. The mixture was cooled, filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in the minimum amount of methylene chloride, the solution was filtered through a short column of silica gel, using a 2:1 v:v mixture of hexane and ether as eluent. The solvents were evaporated. The residue was subjected to high pressure liquid chromatography (HPLC) twice, using an 8:1 v:v mixture of hexane and ether as eluent. The less polar portions thus obtained were combined, the solvents were evaporated and the residue crystallized from methylene chloride/hexane to give N-diphenylmethyl-cis-3-methyl-2-azetidinecarboxylic acid benzyl ester (3E), as a colorless solid, 112°-113.5° C.

Quelle