transfer purchased music from one account on laptop to iphone with a different account

OK peeps. I've read a ton of threads and I don't think this is possible but maybe someone out there has found a workaround.

Here's the scenario. I have a friend whom his "ex" had purchased music on their laptop through her apple ID. That ID is still signed in and authorized for the purchases on the laptop. And I should note he has that ID information. I should also note the laptop is Windows. What he would like to do is simply be able to listen to those songs on HIS iphone but not sign in with her apple ID on his iphone. Is there a way to transfer those songs to his iphone using family sharing or to his account or some other way so that he can listen to those purchases w/o signing into HIS phone with HER apple ID?

I know there are multiple threads on how apple does NOT allow to transfer purchases from one account to another but I have also read many other things on certain types of workarounds for certain scenarios. Any ideas or workarounds will be greatly appreciated.

Thanks.