here is something I pulled up, it isn't mine.
Transfer Music from iTunes to PSP (Free)
Step 1. Create a new playlist in iTunes.
Step 2. Add the protected songs to your playlist until you have 72 minutes of music.
Step 3. Click Edit and select Preferences.
Step 4. Select the Advanced tab.
Step 5. Click the radio button next to Audio CD on the Burning tab.
Step 6. Click the Burn Disc button.
Step 7. Upon completion of burning the disc, rip the songs to MP3 using Windows Media Player.
Step 8. Connect the PSP to your PC with a USB cable.
Step 9. Press the "home" button on the PSP (it's a tiny button to the lower left of the screen) then use the left-right directional buttons to find "Settings", then the up-down buttons to find "USB Connection" on the PSP.
Step 10. Press the "X" button (you got it, the round button with the "X" on it) and your PSP should display "USB Connection".
Step 11. In a moment or two your computer should tell you that a new USB device has been connected, then show you a new generic hard drive, usually E: or F:
Step 12. Click on the drive letter that corresponds to the PSP unit.
Step 13. Now create a new folder on that drive and name it "psp".
Step 14. Within the new "psp" folder create another folder, and name it "music".
Step 15. Copy your desired mp3 files into the new "music" folder.
Step 16. When you're done copying your desired music tracks, press the "O" button on the PSP to get out of USB connect mode.
Now you're ready to go! Use the left-right arrows to move to the music area, then the up-down arrows to find "Memory Stick". Chose that folder by pressing the "X" button again, and you should be able to find all your favorite music!