4-Trimethylsilyl-3-cyanobutanoic acid → 4-Amino-3-[(trimethylsilyl)methyl]butanoic acid

HRID 341338Notes

Reaction equation

HRID 341338 reaction equation
[CH3:1][Si:2]([CH3:12])([CH3:11])[CH2:3][CH:4]([C:9]#[N:10])[CH2:5][C:6]([OH:8])=[O:7]>CO.[OH-].[Pd+2].[OH-]>[NH2:10][CH2:9][CH:4]([CH2:3][Si:2]([CH3:11])([CH3:1])[CH3:12])[CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 781006764-Trimethylsilyl-3-cyanobutanoic acid

Product 1

HCID 706737344-Amino-3-[(trimethylsilyl)methyl]butanoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-(trimethylsilyl)-3-cyanobutanoic acid (178 mg, 0.962 mmol) and palladium hydroxide (20% on carbon, wetted with ca. 50% water, 36 mg) in methanol (10 ml) was subjected to catalytic reduction under a hydrogen atmosphere [0.45 MPa (gauge pressure)] for 48 hours. The reaction mixture was filtered through Celite, the solvent was evaporated, and then the residue was recrystallized to obtain 4-amino-3-(trimethylsilylmethyl)butanoic acid (172 mg, 95%) mentioned in the title as colorless fine prism crystals.

Workup

  1. customfor 48 hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. customthe solvent was evaporated
  4. customthe residue was recrystallized

Sources & evidence

ORD record
ord-fe23023489a748f6973454cb7a6dbb7e
Source dataset
uspto-grants-2014_11
Patent number
US08895769B2

Reaction notes

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