Can we have visa status change as L1B->H1B(COS)->L1B->H1B

[dilips24]

Please help for the below scenario.

1- If Person is working on L1B with Company X. L1B visa valid till Jan/2019
2- Company Y , files H1B for him. H1B gets approved with COS effective Oct/1/2018.
3- Person want to continue working with Company X till last date of his L1B visa validity
4- He moved out of USA and come back on Oct 1 on L1B visa to change his visa status on L1B.
5- What is process to go back on H1B status after Jan/2019 and start working with Company Y ? Is this possible?

Thanks,