Sodium Cyanide → tert-Butyl 1-(1-amino-1-cyanoethyl)-1-cyclopropanecarboxylate

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Reaction Steps

Tert-butyl 1-acetyl-1-cyclopropanecarboxylate (9.21 g, 50.0 mmol) was dissolved into a 7 N ammonia/methanol solution (300 mL). To this solution was added concentrated ammonia water (90 mL), ammonium chloride (53.5 g, 1.00 mmol), and sodium cyanide (4.90 g, 100.0 mmol) under cooling with ice, and subsequently the mixture was stirred at room temperature for 18 hours. The solvent was concentrated under reduced pressure. To the remaining solution was added water (100 mL), and subsequently extracted with dichloromethane (300 mL and 100 mL×2). To the combined organic layer was added anhydrous sodium sulfate to dry. The drying agent was removed by filtration, and the solvent was removed under reduced pressure to obtain 10.15 g of a crude product of the target compound (48.3 mmol, 97%) as light brown oil. The obtained crude product was used for the subsequent reaction without purifying further.

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