Try placing the iPod in Disk Mode and connecting it to your PC. This should keep the iPod from rebooting and mount the iPod as an external volume on your Windows PC viewable from My Computer or Computer. If you can successfully place the iPod into Disk Mode and have it recognized by iTunes, restore it to factory settings.
Putting iPod devices with a Click Wheel into Disk Mode
- If necessary, verify that your iPod has a Click Wheel.
- Before placing the iPod into Disk Mode, verify that it is charged.
- Toggle the Hold switch on and off (set it to Hold, then turn it off again.)
- Press and hold the Menu and Select buttons for at least six seconds, until the Apple logo appears.
- When the Apple logo appears, release the Menu and Select buttons and immediately press and hold the Select and the Play/Pause buttons until the Disk Mode screen appears.
- Connect the iPod to your computer; the screen on the iPod will should say "Do not disconnect".
If you are having difficulty putting your iPod into Disk Mode, set it on a flat surface. Make sure that the finger pressing the Select button is not touching the Click Wheel. Also make sure that you are pressing the Play/Pause button toward the outside of the Click Wheel and not near the center. If you are still unable to put your iPod into Disk Mode, use one finger from one hand to press the Select button, and one finger from the other hand to press the Play/Pause button.
It wouldn't hurt to also try a different USB sync cable to rule out a faulty/damaged cable. Plug the iPod into a high powered USB 2.0 port as well. The iPod may not be receiving enough output from the iPod to stay connected. This means you should unplug all other USB devices as well minus your keyboard and mouse if it's a desktop.