Pregabalin: spot the stereochemistry flaw

Single question

Pfizer's green-chemistry route to pregabalin uses a lipase to resolve a racemic cyanoester, then reduces the nitrile to the primary amine. The reagents and reaction classes are right. Check the absolute configuration of the resolved intermediate.

Lipase-mediated kinetic resolution

(S) vs (R) pregabalin activity

Tracking absolute configuration through a nitrile reduction

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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