(2R,5R)-(-)-trans-2,5-Dimethylpyrrolidine

[dan2097]

Original report by Alex Clark (Bitbucket: aclarkxyz, GitHub: aclarkxyz).

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... is hating on the trans. Take that out and it works.

[dan2097]

Original comment by Daniel Lowe (Bitbucket: dan2097, GitHub: dan2097).

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I think the issue is that the (2R,5R) already fully specified the stereochemistry making the trans redundant and hence when it comes to apply it no unset stereocentres are found. (2R)-(-)-trans-2,5-Dimethylpyrrolidine is interpretable. trans-2,5-Dimethylpyrrolidine is also interpretable, but arbitrarily gives the other enantiomer.

[dan2097]

Original comment by Alex Clark (Bitbucket: aclarkxyz, GitHub: aclarkxyz).

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Indeed. Now as to whether or not that's a fatal bug... your call!