Ammonium formate → HCID 70673729, compound

HRID 341332Notes

Reaction equation

HRID 341332 reaction equation
[N+:1]([CH2:4][CH:5]([Si:17]([CH3:20])([CH3:19])[CH3:18])[CH2:6][C:7]([O:9]CC1C=CC=CC=1)=[O:8])([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][CH2:4][CH:5]([Si:17]([CH3:18])([CH3:20])[CH3:19])[CH2:6][C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 70673606HCID 70673606, compound

Product 1

HCID 70673729HCID 70673729, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of benzyl 4-nitro-3-(trimethylsilyl)butanoate (797 mg, 2.70 mmol) and palladium/carbon (10%, 165 mg) in methanol (30 ml) was added with ammonium formate (1.70 g, 27.0 mmol), and the mixture was stirred under an argon atmosphere for 40 hours. The reaction mixture was filtered through Celite, and the Celite layer was washed with methanol. The reaction mixture was concentrated under reduced pressure, and the residue was purified by recrystallization and silica gel chromatography [methanol (10 to 25%)/chloroform] to obtain 4-amino-3-(trimethylsilyl)butanoic acid (406 mg, 86%) mentioned in the title as colorless powder.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe Celite layer was washed with methanol
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by recrystallization and silica gel chromatography [methanol (10 to 25%)/chloroform]

Sources & evidence

ORD record
ord-4da1b9521dad4bc6b35897948c716102
Source dataset
uspto-grants-2014_11
Patent number
US08895769B2

Reaction notes

Loading…