(+/-)-Tert-butyl 2-[3-(benzylamino)-4-chlorobenzyl]-2-methylbutanoate → (+/-)-Tert-butyl 2-(3-amino-4-chlorobenzyl)-2-methylbutanoate

HRID 1476099Notes

Reaction equation

HRID 1476099 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:12][C:13]([CH3:23])([CH2:21][CH3:22])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:12][C:13]([CH3:23])([CH2:21][CH3:22])[C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15]

Participants

4

Reactant 1

HCID 58288180(+/-)-Tert-butyl 2-[3-(benzylamino)-4-chlorobenzyl]-2-methylbutanoate

Product 1

HCID 58288184(+/-)-Tert-butyl 2-(3-amino-4-chlorobenzyl)-2-methylbutanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.20 g (about 5.67 mmol) of (+/−)-tert-butyl 2-[3-(benzylamino)-4-chlorobenzyl]-2-methylbutanoate were dissolved in 130 ml of ethyl acetate, and 100 mg of palladium on carbon (10%) were added. At RT, the reaction mixture was stirred under an atmosphere of hydrogen at atmospheric pressure overnight. The reaction mixture was then filtered off with suction through kieselguhr, the residue was washed thoroughly with ethyl acetate and the combined filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1 to 30:1). This gave 924 mg (54.7% of theory) of the target compound.

Workup

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. washthe residue was washed thoroughly with ethyl acetate
  3. concentrationthe combined filtrate was concentrated
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1 to 30:1)

Sources & evidence

ORD record
ord-eadd34cb60cd41b09c4e73151603998c
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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