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3-(Benzyl-methyl-amino)-butyric acid methyl ester → Methyl 3-(methylamino)butanoate

HRID 480248
Notes
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Reaction equation

HRID 480248 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH:5]([N:7](CC1C=CC=CC=1)[CH3:8])[CH3:6]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH:5]([NH:7][CH3:8])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 232160883-(Benzyl-methyl-amino)-butyric acid methyl ester

Product 1

HCID 12636115Methyl 3-(methylamino)butanoate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

3-(Benzyl-methyl-amino)-butyric acid methyl ester (15 g, 67.8 mmol, 1.0 equiv) was placed in a Parr hydrogenation bottle and dissolved in 50 mL of MeOH. 20% Palladium hydroxide on carbon (0.5 g, 0.94 mmol, 0.014 equiv) was added and the mixture was shaken at 50 psi H2 for 16 h. The reaction was judged as complete when the uptake of H2 had stopped. The bottle was opened and 10 g of diatomaceous earth in 100 mL of MeOH was added. The mixture was filtered on a pad of diatomaceous earth which was then washed with 2×100 mL of MeOH. The filtrates were combined and concentrated in vacuo to yield the desired product as an oil that is somewhat volatile (7.6 g, 85%). The crude product was used without further purification; MS, m/z 132=M+1.

Workup

  1. filtrationThe mixture was filtered on a pad of diatomaceous earth which
  2. washwas then washed with 2×100 mL of MeOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95867b2c82474370a76bd2b91692c3a7
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06649642B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes