Here's a more explicitly worked out version of my comment above. Consider $P(\sin nx)=\sin 2^n x$. This is an isometry, so in particular bounded in $L^2(0,\pi)$. It can not be approximated in the desired way.
Indeed, suppose we had an operator $Q$ with $\|P-Q\|<\epsilon$ that is also bounded on $H^1$. Since $\|\sin nx \|_{H^1}\simeq n$, this would have to map to functions $g=Q(\sin nx)$ with $\|g'\|_2\lesssim n$. However, we also have $\|g-\sin 2^n x\|_2<\epsilon$. This is not possible because the second inequality forces $g$ to mimic the oscillations of $\sin 2^n x$, but that will make $\|g'\|_2$ too large.
We have approximately $2^n$ intervals, of size $\simeq 2^{-n}$ each, on which $\sin 2^n x\ge 3/4$. If we had $g(x)\le 1/4$ throughout such an interval $I$, then $\|g-\sin 2^nx\|^2_{L^2(I)}\gtrsim 2^{-n}$. Thus we can have at most $\simeq \epsilon 2^n$ such intervals.
In other words, for a fraction close to one (as $\epsilon\to 0$) of the $2^n$ intervals where $|\sin 2^n x|\ge 3/4$, the function $g$ will also take a corresponding value $|g|\ge 1/4$ on these intervals. So $g$ oscillates between $\pm 1/4$ at least $\gtrsim 2^n$ times.
However, when $g$ changes from $1/4$ to $-1/4$ on $J$, then
$$
\frac{1}{2} \le \int_J |g'| \le \|g'\|_{L^2(J)} |J|^{1/2} ,
$$
and thus in particular $\|g'\|^2_{L^2(J)}\gtrsim 1$. Since we have $\simeq 2^n$ such intervals, $\|g'\|_2$ comes out much too large.