N-((1R)-1-benzyl-2-(benzylamino)ethyl)-N-methylcarbamic acid tert-butylester → N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester

HRID 495832Notes

Reaction equation

HRID 495832 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([C@H:9]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10][NH:11]CC1C=CC=CC=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:26])[N:7]([C@@H:9]([CH2:10][NH2:11])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 54122148N-((1R)-1-benzyl-2-(benzylamino)ethyl)-N-methylcarbamic acid tert-butylester

Product 1

HCID 53810010N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylesterYield 25.3%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

A suspension of 20% palladium hydroxide on charcoal (4.63 g) and N-((1R)-1-benzyl-2-(benzylamino)ethyl)-N-methylcarbamic acid tert-butylester (4.40 g, 12.4 mmol) was kept for 8 h under a hydrogen atmosphere at (pressure: 1 atm). The reaction mixture was flushed with nitrogen and filtered through a plug of celite. The solvent was removed. The crude product was purified by flash chromatography on silica (110 g), using dichloromethanelmethanol/25% aqueous ammonia as eluent, to give 830 mg of N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester.

Workup

  1. customThe reaction mixture was flushed with nitrogen
  2. filtrationfiltered through a plug of celite
  3. customThe solvent was removed
  4. customThe crude product was purified by flash chromatography on silica (110 g)

Sources & evidence

ORD record
ord-f02be50ed8544356a55b7ef16167e1b5
Source dataset
uspto-grants-2005_09
Patent number
US06939880B2

Reaction notes

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