Are there any methods to selectively protect an amino group, preferably with mesyl/tosyl chloride (or other sulfonyl chloride) if an alcohol group is present?
Serapinas,
A 2,2-Bis(ethoxycarbonyl) vinyl- (BECV) group was used for the selective protection of amines at room temperature in the presence of potentially interfering functional groups such as OH, SH, COOH, see
---Ilangovan, Andivelu; Kumar, Rajendran Ganesh, Chemistry (2010)- A European Journal 16, 2938-2943.
Good luck
u can use tertiary butyl bromoacetate also to protect primary amine by keeping alcohol group free.
Hi. If you amine is primary (as you refer to amino group) I think that you should not have any problems to protect the amine selectively in the presence of OH. I think any protecting group other then silyl-based will preferentially react with NH2 - for example BOC.
Good luck
The amino group is inherently more nucleophilic. Run the reaction at room temperature with a weak base to mop up acid produced. Take your amino alcohol, dissolve in DCM heterogenous in the presence of NaHCO3 or K2CO3 etc, and add 1 e.q. of TsCl or MsCl then stir o/n.
It is probably quicker to just try the reactions out.
Amines can be selectively protected by benzyl chloroformate of BOC anhydride. with these reagents, amine will form carbamate and hydroxy will form carbonate. The carbonate will get hydrolyzed during aqueous work up and you will have protected amino group.
Hello, Boc protection of secundary amine in presence of primary alcohol works perfect.