Tert-butyl 2-cyano-2,2-dimethylacetate → Tert-butyl 3-amino-2,2-dimethylpropanoate

HRID 1480958Notes

Reaction equation

HRID 1480958 reaction equation
[C:1]([O:5][C:6](=[O:12])[C:7]([C:10]#[N:11])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([O:5][C:6](=[O:12])[C:7]([CH3:9])([CH3:8])[CH2:10][NH2:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 53834489Tert-butyl 2-cyano-2,2-dimethylacetate

Product 1

HCID 15430260Tert-butyl 3-amino-2,2-dimethylpropanoateYield 92.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of cyano-dimethyl-acetic acid tert-butyl ester (5.3 g) and Raney Ni (2 mL in water) in MeOH (400 mL) was stirred at rt under H2 atmosphere (balloon) overnight. Then the reaction mixture was filtered over Celite pad, filtrate was concentrated to give the desired product (5 g). 1H NMR in CDCl3, δ in ppm: 2.8 (br, 2H), 1.45 (s, 9H), 1.17 (s, 6H).

Workup

  1. filtrationThen the reaction mixture was filtered over Celite pad, filtrate
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-7419d1b1112e4b1f9e5e5ffa7d83e30d
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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