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

HRID 1675190Notes

Reaction equation

HRID 1675190 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]>[Ni].C(O)C>[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

4

Reactant 1

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

Product 1

HCID 57434367Tert-butyl 1-(1,2-diamino-1-methylethyl)-1-cyclopropanecarboxylateYield 74%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To an ethanol solution (50 mL) of tert-butyl 1-(1-amino-1-cyanoethyl)-1-cyclopropanecarboxylate (1.12 g, 5.30 mmol) was added an ethanol suspension (30 mL) of Raney Nickel catalyst (R-100 manufactured by NIKKO RICA CORPORATION, 10 mL), and the mixture was stirred vigorously under hydrogen atmosphere at room temperature for 6 hours. The catalyst was removed by filtration through celite, and the solvent was removed under reduced pressure to obtain 0.84 g of a crude product of the target compound (3.92 mmol, 74%) as transparent and colorless oil. The obtained crude product was used for the subsequent reaction without further purification.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ab055458db5940a8a50cfe9e4d56976c
Source dataset
uspto-grants-2011_08
Patent number
US08003666B2

Reaction notes

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