tert-butyl (1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexylcarbamate → (1r,2s)-2-Amino-n-(cyanomethyl)cyclohexanecarboxamide

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Reaction Steps

The nitrile compound of step 3 (5.82 g, 20.68 mmol) was dissolved in 69 mL (0.3M) of formic acid and stirred at room temperature for 5 h to completion. The formic acid was evaporated and the residue partitioned between ethyl acetate and 1 N sodium hydroxide, repeating the extraction three times with fresh ethyl acetate. The organic layers were combined, dried over magnesium sulfate and concentrated to give 2.22 g of the crude (1R,2S)-2-amino-N-(cyanomethyl)cyclohexanecarboxamide.

Provenance & Evidence