Fixpoint upd (i : nat) {A} new (l : list A) : option (list A) :=
  match i, l with
  | O, _ :: l => Some (new :: l)
  | _, nil => None
  | S i, x :: l =>
    match upd i new l with
    | Some l' => Some (x :: l')
    | None => None
    end
  end.

Lemma upd_lt {A} i x l : @upd i A x l <> None <-> lt i (length l).