Problem syncing iPod with my external hard drive!

Recently I transfered my entire iTunes library over to my external HDD and completed all of the necessary requirements to be able to play my music back from the new folder location (i.e. changed the location in iTunes preferences and consolidated everything etc)
Now I have gone to sync my iPod Touch with iTunes and it keeps coming up with an error and won't sync my music. Everything plays just fine on iTunes itself, I just can't get the music onto my iPod and actually sync with my external HDD.
So far I have tried exiting iTunes, changing USB ports and reconnecting my hard drive, all to no avail..

::  Attemping to copy to the disk "My Passport" failed.  An unknown error occurred (-54)
Tim DawsonIT ManagerAsked:
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Tim DawsonConnect With a Mentor IT ManagerAuthor Commented:
Well it turns out the problem was my c drive did not have enough room.  Since it would not go to the external drive, I moved other data to the external and let it save internal.   Funny, the ITunes library will go to the external drive but not the back up.    Anyway it works.
Thanks
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Tim DawsonIT ManagerAuthor Commented:
Actually its an iPhone,  if that makes a difference.
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Steven WallaceManaged Services ManagerCommented:
What version of iTunes? What operating system are you using?
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Tim DawsonIT ManagerAuthor Commented:
Windows 10  
IOS 10.0.2
Latest ITunes version.
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Steven WallaceManaged Services ManagerCommented:
What are steps you doing to make it sync via USB?

Have you tired syncing via WiFi? https://support.apple.com/en-au/HT203075
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Tim DawsonIT ManagerAuthor Commented:
Just plug it in.  It recognizes it but then fails because of the external hard drive.

I'll try WiFi ..........
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William FulksSystems Analyst & WebmasterCommented:
Unplug both, then plug the hard drive in first. Wait for it to spin up where you can read files and such, then plug in the iPhone and try it.
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Tim DawsonIT ManagerAuthor Commented:
Just had to do a workaround.
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