Reaction #7392

Reaction equation

tert-butyl 2-amino-butanoate

ethyl 2-azido-4-bromo-butanoate

triethylamine

→

title compound

Yield 52.5%

Ethyl 2-azido-4-{[1-(tert-butoxycarbonyl)propyl]amino}butanoate

Yield 52.5%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   Otherevaporated onto silica gel (Merck.7734)
3. 3
   OtherThe pre-absorbed material was purified by flash column chromatography (Merck. 9385, eluting with cyclohexane:ethyl acetate 6:1)

Procedure

To a solution of tert-butyl 2-amino-butanoate (0.397 g) and ethyl 2-azido-4-bromo-butanoate (0.286 g) in acetonitrile (5 ml) was added triethylamine (0.347 ml). The mixture was heated at 50° C. for 18 h, cooled and evaporated onto silica gel (Merck.7734). The pre-absorbed material was purified by flash column chromatography (Merck. 9385, eluting with cyclohexane:ethyl acetate 6:1) to give the title compound (0.200 g) as a mixture of four diastereomers.

Source