The discovery via gravitational waves of binary black hole systems with total masses greater than $60M_odot$ has raised interesting questions for stellar evolution theory. Among the most promising formation channels for these systems is one involving a common envelope binary containing a low metallicity, core helium burning star with mass $sim 80-90M_odot$ and a black hole with mass $sim 30-40M_odot$. For this channel to be viable, the common envelope binary must eject more than half the giant stars mass and reduce its orbital separation by as much as a factor of 80. We discuss issues faced in numerically simulating the common envelope evolution of such systems and present a 3D AMR simulation of the dynamical inspiral of a low-metallicity red supergiant with a massive black hole companion.
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