2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester → 2-Aminomethyl-4,4,8-trimethyl-nonanoic acid

HRID 2216689Notes

Reaction equation

HRID 2216689 reaction equation
C([O:8][C:9](=[O:23])[C:10]([C:21]#[N:22])=[CH:11][C:12]([CH3:20])([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])C1C=CC=CC=1.[H][H]>C1COCC1.CO.[NH4+].[OH-].[Pd].[Ni]>[NH2:22][CH2:21][CH:10]([CH2:11][C:12]([CH3:19])([CH3:20])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])[C:9]([OH:23])=[O:8]

Participants

7

Reactant 2

HCID 688724612-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl esterHCID 178418361HCID 178418361, compound2×

Product 1

HCID 103079982-Aminomethyl-4,4,8-trimethyl-nonanoic acidYield 16.9%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 21894508Ammonium hydroxide methanolSolvent

Procedure

2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester (1.3 g, 4.14 mmol) in THF (50 mL) was treated with hydrogen in the presence of 20% Pd/C to give a mixture of the cyano acid and the cyano methyl ester. The mixture was purified by silica gel chromatography to give 278 mg of cyano acid. The acid was then treated with hydrogen in the presence of Raney Ni in MeOH/NH4OH to give 0.16 g of 2-aminomethyl-4,4,8-trimethyl-nonanoic acid. m/z 230.3 (M+).

Workup

  1. customto give
  2. customThe mixture was purified by silica gel chromatography
  3. customto give 278 mg of cyano acid

Sources & evidence

ORD record
ord-e27afb26970542839b2b6d4f2753935a
Source dataset
uspto-grants-2006_09
Patent number
US07112610B2

Reaction notes

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