[ideamon]

Hello,

I have got reagent trifenylfosfine PS resin  ... i tried to use it in Mitsunobu reaction and reduction of azide, but i detected a difficult of conversion. Reactions are very slow and even with 2-3 equivalents conversion by TLC maximum is ­~70%.
Maybe someone have worked with it and know some specificity or something  ..

Thank you!   

[discodermolide]

Hello,

I have got reagent trifenylfosfine PS resin  ... i tried to use it in Mitsunobu reaction and reduction of azide, but i detected a difficult of conversion. Reactions are very slow and even with 2-3 equivalents conversion by TLC maximum is ­~70%.
Maybe someone have worked with it and know some specificity or something  ..

Thank you!   

Try using triphenylphosphine itself.
Azide to amine? Hydrogenation

[ideamon]

I have tried  trifenylfosfine itself, and reactions go wonderful....but i have to think of a technology to prepare in big scale and with no chromatography. 

[discodermolide]

I have tried  trifenylfosfine itself, and reactions go wonderful....but i have to think of a technology to prepare in big scale and with no chromatography. 

The resin is no good for large scale. It gets broken up by the stirrer. Consequently you can't filter it off or the filtration is very slow.
Depending on your product you can crystsallise the Ph3P=O from the mixture.
You could also hydrolyze the esters and extract the phosphine oxide out. Likewise with the amines, make the HCl salt and extract.