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Used a 3/8" hex key to remove the crank but the outer bolt needs to be tightened separately. Perhaps it's possible to tighten it with the crank off or do I need a special pin type tool. Its a ~2008 Cannondale Synapse Carbon. Hollow shaft running to the opposite crank arm.

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    You may be able to use a two-pin adjustable BB tool. That search pulls up a lot of images of the tool I'm thinking of, and they're available right down to $5 or so
    – Móż
    Commented Apr 25, 2016 at 3:41

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You may be able to use a two-pin adjustable BB tool. That search pulls up a lot of images of the tool I'm thinking of, and they're available right down to $5 or so

enter image description here

(from my comment since we haven't got a better answer)

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