In finding this residue, I took a Taylor expansion of $\sin(x)$ and substituted in $\tan(z)$ and then attempted to compute the residues of the odd powers of $\tan(z)$ at $z=\frac{\pi}{2}$. Using Wolfram Alpha, it seemed to be that: \begin{equation} \operatorname{Res}(\tan^{2n-1}(z), \frac{\pi}{2}) = (-1)^n \end{equation} Giving the residue of $\sin(\tan(z))$ as $-\sinh(1)$.
Is this correct?
Also, I was unable to show $\operatorname{Res}(\tan^{2n-1}(z), \frac{\pi}{2}) = (-1)^n$.
Is this true and if so any hints on how to show it?
Using $\sin\tan z=\sum_{n\geq 0}\frac{(-1)^n}{(2n+1)!}\left(\tan z\right)^{2n+1}$ is a good idea. Then $$ \operatorname*{Res}_{z=\pi/2}\left(\tan z\right)^{2n+1}= -\operatorname*{Res}_{z=0}\left(\cot z\right)^{2n+1}=-\frac{1}{2\pi i}\oint_{\|z\|=\varepsilon}\left(\cot z\right)^{2n+1}\,dz$$ by Cauchy's integral formula. The substitution $z=\arctan u$ allows to write the RHS as $$ -\frac{1}{2\pi i}\oint_{\|u\|=\varepsilon}\frac{du}{(u^2+1)u^{2n+1}}=-\operatorname*{Res}_{u=0}\frac{1}{u^{2n+1}}\left(1-u^2+u^4-u^6+\ldots\right) $$ hence $$ \operatorname*{Res}_{z=\pi/2}\left(\tan z\right)^{2n+1}= (-1)^{n+1}, $$ $$\operatorname*{Res}_{z=\pi/2}\sin\tan z=-\sum_{n\geq 0}\frac{1}{(2n+1)!}=-\sinh(1).$$