tert-Butyl 1-(1-amino-1-cyanoethyl)-1-cyclopropanecarboxylate → Tert-butyl 1-(1,2-diamino-1-methylethyl)-1-cyclopropanecarboxylate

HRID 229508Notes

Reaction equation

HRID 229508 reaction equation
[NH2:1][C:2]([C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1)([C:4]#[N:5])[CH3:3]>C(O)C.[Ni].[H][H]>[NH2:1][C:2]([C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]1)([CH3:3])[CH2:4][NH2:5]

Participants

5

Reactant 1

HCID 57434366tert-Butyl 1-(1-amino-1-cyanoethyl)-1-cyclopropanecarboxylate

Product 1

HCID 57434367Tert-butyl 1-(1,2-diamino-1-methylethyl)-1-cyclopropanecarboxylate

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 178418361HCID 178418361, compoundSolvent

Procedure

To a solution (50 mL) of tert-butyl 1-(1-amino-1-cyanoethyl)-1-cyclopropanecarboxylate (1.12 g, 5.30 mmol) in ethanol was added a suspension (30 mL) of Raney nickel catalyst (R-100 manufactured by Nikko Rica Corporation, 10 mL) in ethanol, and the suspension was vigorously stirred at room temperature for 6 hours in hydrogen gas atmosphere. The catalyst was removed by filtration through celite, and the solvent was removed by distillation under reduced pressure to obtain 0.84 g (3.92 mmol, 74%) of the crude target compound as a colorless transparent oil. The thus obtained crude product was used in the subsequent reaction with no further purification.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe solvent was removed by distillation under reduced pressure
  3. customto obtain 0.84 g (3.92 mmol, 74%) of the crude target compound as a colorless transparent oil
  4. customThe thus obtained crude product
  5. customwas used in the subsequent reaction with no further purification

Sources & evidence

ORD record
ord-c6be1e322053426eb8318f6356384eb7
Source dataset
uspto-grants-2009_07
Patent number
US07563805B2

Reaction notes

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