Ethyl 2-Cyano-2-methylpropionate → Ethyl 3-amino-2,2-dimethylpropanoate

HRID 713906Notes

Reaction equation

HRID 713906 reaction equation
[C:1]([C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]>C(O)C.[OH-].[NH4+].[Ni]>[NH2:2][CH2:1][C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 344887Ethyl 2-Cyano-2-methylpropionate

Product 1

HCID 421529Ethyl 3-amino-2,2-dimethylpropanoateYield 70.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22731726Ethanol ammonium hydroxideSolvent

Procedure

To a solution of ethyl 2-cyano-2-methylpropanoate (0.6 g, 4.2 mmol, 1.0 equiv) in 6 mL of ethanol/ammonium hydroxide (10:1) was added Ra/Ni (20%, 0.12 g). The resulting mixture was stirred under hydrogen at r.t. for 16 h. The catalyst was filtered off, and the filtrate was concentrated to give ethyl 3-amino-2,2-dimethylpropanoate (0.43 g, yield: 70%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ: 4.15 (q, 2H), 2.77 (s, 2H), 1.76 (s, 2H), 1.26 (t, 3H), 1.18 (s, 6H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c58ac89519e4076bf7d1f76e894025c
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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