Triphenylphosphine → HCID 22182456, compound

Participants

Reaction Conditions

Reaction Steps

4-Benzyloxy-N-[2-(2-hydroxy-ethylamino)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propyl]-benzenesulfonamide (compound of formula XLIV, 10.6 g, 21.5 mmol) was diluted with tetrahydrofuran (400 ml) and cooled to about 0° C. prior to the addition of triphenylphosphine (6.69 g, 25.5 mmol) and diethylazodicarboxylate (4.2 ml, 26.7 mmol). The mixture was allowed to stir at about 0° C. for about 2 hours then was concentrated in vacuo and diluted with ethyl acetate and extracted with water. The organic layer was dried with sodium sulfate and concentrated in vacuo. Silica gel chromatography using ethyl acetate followed by 10% methanol in chloroform containing 0.1% ammonium hydroxide gave 6.8 g of a compound of formula XLV.

Provenance & Evidence