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

HRID 446070Notes

Reaction equation

HRID 446070 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-578cb05bb06e409f939f6cdf2b39de97
Source dataset
uspto-grants-2013_07
Patent number
US08476429B2

Reaction notes

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