2-(4-Cyano-3-fluoro-phenoxy)-propionic acid tert-butyl ester → (+)-2-(4-Aminomethyl-3-fluoro-phenoxy)-propionic acid tert-butyl ester

HRID 350976Notes

Reaction equation

HRID 350976 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[C:12]([F:18])[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:19])[CH:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[C:12]([F:18])[CH:11]=1)[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 235293652-(4-Cyano-3-fluoro-phenoxy)-propionic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 23529364(+)-2-(4-Aminomethyl-3-fluoro-phenoxy)-propionic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(±)-2-(4-Cyano-3-fluoro-phenoxy)-propionic acid tert-butyl ester (1.77 g, 6.7 mmol) was shaken on a Parr shaker under 40 psi hydrogen for 30 min, using palladium hydroxide on carbon (1 g, 30% Pd by wt) in 200 mL anhydrous methanol. The reaction mixture was filtered through sintered glass, and solvents removed in vacuo to afford 1.71 g colorless oil (95% yield).

Workup

  1. filtrationThe reaction mixture was filtered through sintered glass, and solvents
  2. customremoved in vacuo

Sources & evidence

ORD record
ord-9febfc997ad1461b942f4072c3052b5a
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

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