An man convicted of murdering a woman after breaking into her apartment as she slept was put to death Thursday evening in Alabama in the nation’s fourth execution using nitrogen gas.

A federal judge on Friday refused to stop what would be the fourth nitrogen gas execution in the U.S., saying the inmate had not proven his claims that the new method is unconstitutionally cruel and causes psychological terror.

Frazier was convicted of capital murder for breaking into a Birmingham woman's apartment, stealing cash, raping her at gunpoint, and killing her.