Tert-butyl 2-(benzylamino)-2-methylpropanoate → tert-Butyl 2-methylalaninate

HRID 572558Notes

Reaction equation

HRID 572558 reaction equation
C([NH:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[NH2:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 66652853Tert-butyl 2-(benzylamino)-2-methylpropanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 7019940tert-Butyl 2-methylalaninate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of tert-butyl 2-(benzylamino)-2-methylpropanoate (20 g, 0.08 mol) in ethyl acetate (1 L), was added the catalyst Palladium-carbon (10%, 2.2 g). The resulting mixture was put under the hydrogen pressure of 5 Kg/cm2, at RT for 18 h. The reaction mixture was filtered. The filtrate was concentrated affording the title compound as pale green liquid. 1H NMR (DMSO-d6, 400 MHz) δ 1.38 (brs, 2H), 1.14 (s, 9H), 1.14-1.11 (d, J=10.7 Hz, 6H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b1bebc538e1945129244d79600c4a511
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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