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1
With a sharp knife, cut the skin off the pineapple, then cut the pineapple into 6 lengthwise wedges. Remove the core. (Alternatively cut your pineapple into rings or chunks if you wish a different shape than the wedges).
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2
Bring 4 cups of water and 3/4 cup of the white sugar to a boil in a medium sized sauce pan. Add the pineapple. If necessary add a bit more water to cover the pineapple pieces. Lower the heat and cook for 20 minutes or until the pineapple is tender but not to soft. (Note that the cooking time with be less if you use the smaller pineapple chunks or rounds so keep and eye on it).
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3
Remove the pineapple from the syrup using tongs and place the pineapple into a large squat glass jar or bowl. (Do not use metal).
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4
Return the syrup to the heat and bring to a near boil. Continue to cook the syrup to reduce it until you have 2 cups remaining. Pour the syrup reduction through strainer over the pineapple. Let it marinate overnight.
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5
The next day remove the pineapple from the poaching liquid. Return the poaching liquid to the stove and further reduce it over medium high heat until one cup remains. Once it is reduced, remove from heat, add the 1 tsp of butcher grind black pepper. Let the reduction cool.
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6
Place the pineapple on a baking sheet and sprinkle heavily with the remain 1/4 cup white sugar. Broil until the pineapple begins to caramelize. Turn pineapple pieces and broil the remaining side(s) for 1 minute.
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7
Serve with vanilla ice cream and top with the Black Pepper Syrup.
