Take a look at this reaction scheme:

http://www.organic-chemistry.org/abstracts/lit3/507.shtm

After the formation of the amide bond reduction using LiAlH4 will result in a secondary amine.

Alternatively, you can look for other generic approaches that involve the amidation of ester bonds. This the reaction produces an amide bond as shown these can always be reduced to amine via LiAlH4, albeit, LiAlH4 will also reduce other oxygen types of bonds to alcohol groups.

aminolyzed with 1,6-hexanediamine to introduce free amino groups

First convert an ester into amide on treatment with  ammonia & then reduce amide  by LiAlH4 in Dry ether.