rac-tert-Butyl (2-cyanopentan-2-yl)carbamate 2-methylpropan-2-ol → rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamate

HRID 1486317Notes

Reaction equation

HRID 1486317 reaction equation
[C:1]([C:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])([CH2:5][CH2:6][CH3:7])[CH3:4])#[N:2].CC(O)(C)C>CO.[Ni]>[NH2:2][CH2:1][C:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:4])[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 131736783rac-tert-Butyl (2-cyanopentan-2-yl)carbamate 2-methylpropan-2-ol

Product 1

HCID 84723920rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

61.0 g (212.98 mmol) of rac-tert-butyl (2-cyanopentan-2-yl)carbamate-2-methylpropan-2-ol from Example 151A were dissolved in 618 ml of 7 N ammoniacal methanol and admixed under argon with 66 g of Raney nickel (50% aqueous slurry). Subsequently, the reaction mixture was hydrogenated in an autoclave at 20-30 bar overnight. The reaction mixture was filtered through Celite, rinsed well with methanol and concentrated. 43.70 g (95% of theory) of the target compound were obtained.

Workup

  1. customwas hydrogenated in an autoclave at 20-30 bar overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. washrinsed well with methanol
  4. concentrationconcentrated
  5. custom43.70 g (95% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-36e6f2c7e8784d61960655ce531f63ae
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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