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

HRID 1675189Notes

Reaction equation

HRID 1675189 reaction equation
[C:1]([C:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5]1)(=O)[CH3:2].[NH3:14].CO.[Cl-].[NH4+:18].[C-:19]#N.[Na+]>O.N>[NH2:14][C:1]([C:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5]1)([C:19]#[N:18])[CH3:2]

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 21705897Ammonia methanolHCID 57434365tert-Butyl 1-acetylcyclopropanecarboxylate

Product 1

HCID 57434366tert-Butyl 1-(1-amino-1-cyanoethyl)-1-cyclopropanecarboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 12896473Azane;hydrateSolvent

Procedure

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.

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe solvent was concentrated under reduced pressure
  3. additionTo the remaining solution was added water (100 mL)
  4. extractionsubsequently extracted with dichloromethane (300 mL and 100 mL×2)
  5. additionTo the combined organic layer was added anhydrous sodium sulfate
  6. customto dry
  7. customThe drying agent was removed by filtration
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-907c62fdc9984d5bb698100709749917
Source dataset
uspto-grants-2011_08
Patent number
US08003666B2

Reaction notes

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