Yes. But the problem is that he will be out of status after Oct.1 (The H1 status will overwrite the OPT, and the h1 then will also be invalid because he lost the job). Of course, if he can find a job in one or two months after Oct. 1, he still can do H1 transfer and have a chance to get it approved with I-94 or without I-94 (he needs to get an H1 visa to activate it outside US in this case).