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

tert-Butyl 1-acetyl-1-cyclopropanecarboxylate (9.21 g, 50.0 mmol) was dissolved in a 7N solution of ammonia in methanol (300 mL), and to this solution in an ice bath were added concentrated ammonia solution (90 mL), ammonium chloride (53.5 g, 1.00 mol), and sodium cyanide (4.90 g, 100.0 mmol). The mixture was stirred at room temperature for 18 hours, and the solvent was concentrated under reduced pressure. To the concentrate was added water (100 mL), and the solution was extracted with dichloromethane (300 mL+2×100 mL). The organic layers were combined, and dried by adding anhydrous sodium sulfate. After removing the dessicating agent by filtration, the solvent was removed by distillation under reduced pressure to obtain 10.15 g (48.3 mmol, 97%) of the crude target compound as a pale brown oil. The thus obtained crude product was used in the subsequent reaction with no further purification.

1. concentrationthe solvent was concentrated under reduced pressure
2. additionTo the concentrate was added water (100 mL)
3. extractionthe solution was extracted with dichloromethane (300 mL+2×100 mL)
4. customdried
5. additionby adding anhydrous sodium sulfate
6. customAfter removing the dessicating agent
7. filtrationby filtration
8. customthe solvent was removed by distillation under reduced pressure
9. customto obtain 10.15 g (48.3 mmol, 97%) of the crude target compound as a pale brown oil
10. customThe thus obtained crude product
11. customwas used in the subsequent reaction with no further purification

ORD record

ord-c7f2952ea8f94f9580ae03198bb033c6

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476429B2