try using the ipod as a hard drive (i think you can do this with tthe nano)..if you cant see it on the windows explorer windows ..go to folder options and have it reveal all hidden folders…..know that for a touch you cant do taht unless you have the touch jailbroken and have open ssh and winscp

1)open Itunes
2)open preferences on Itunes
3)open my computer
4)plug in Ipos
5)go to Ipod in my computer
6)copy music folder
7)paste somewhere else in your computer, not under Itunes
8)unplug Ipod, using safely remove hardware in lower right corner on toolbar
9)close my computer
10)close Itunes preferences
11)File>add folder to library
12)go to music folder from ipod, double click it
13)listen to music
it’s been a while, i’m 99% sure thats it.if there’s some subtlety i missed, go to apple.com, get to the answers part (that is similar to this one) and search for your question. after much searching, you will find it

iPod sólo puede sincronizar con un ordenador de iTunes. iTunes bloquea esta función ya que iTunes es la herramienta con una forma de transferir los archivos de iTunes al iPod. usted debe utilizar otras herramientas para conseguirlo. Hay par de herramientas para la transferencia de archivos entre el iPod y el ordenador (para la copia de seguridad) depende de sus exigencias, por ejemplo, la transferencia sólo canciones / vídeos, transferir fotos etc Puede echar un vistazo por debajo de la revisión del sitio, espero que útiles.

You need iPod to itunes Transfer to transfer your songs/videos to itunes,try Cucusoft iPod/iPhone to itunes Transfer,
it is a very handy tool for windows user to transfer music songs, playlists, video files and more from iTunes to Computer. Download at
GOOD LUCK!