Got to many ways...
Print 1-300 simplex, one copy, (reverse page order(?))
Flip the pages back into the paper tray
Print page 301, 300 copies
With a RIP driven printer capable of Variable Data Printing, store page 301 in the RIP, VDP, print on back
Print pages 1-300, use VDP stored page
Perhaps with Indesign, use a Scott Zanelli's Place Multiple Page script
Facing Pages document, place 1-300 on the left hand pages. Place page 301 on the right hand Master page,