For the Simple Syrup: Makes about 2 cups
Combine the Monk Fruit in the Raw, grapefruit juice, peppercorns, and rosemary in a medium saucepan. Bring to a simmer over medium heat and cook for 5 minutes. Remove from heat and allow to sit for 20 minutes. Strain the mixture and discard solids. Cool completely. Store leftovers in an airtight container for up to 1 week.
For the Cocktail:
Combine the bourbon and simple syrup in a shaker with ice and shake to combine. Pour over ice in a highball glass or other small glass and top with club soda. Top with pepper. Serve.