(5-{2-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-propyl}-benzo[1,3]dioxol-2-ylmethyl)-carbamic Acid Benzyl Ester → N-[2-(2-aminomethyl-benzo[1,3]dioxol-5-yl)-1-methyl-ethyl]-N-ethyl-2,2,2-trifluoro-acetamide

HRID 1828975Notes

Reaction equation

HRID 1828975 reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[O:16][C:15]2[CH:17]=[CH:18][C:19]([CH2:21][CH:22]([N:24]([CH2:31][CH3:32])[C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH3:23])=[CH:20][C:14]=2[O:13]1)C1C=CC=CC=1>[Pd].CO>[NH2:10][CH2:11][CH:12]1[O:16][C:15]2[CH:17]=[CH:18][C:19]([CH2:21][CH:22]([N:24]([CH2:31][CH3:32])[C:25](=[O:30])[C:26]([F:28])([F:27])[F:29])[CH3:23])=[CH:20][C:14]=2[O:13]1

Participants

4

Reactant 1

HCID 86595988(5-{2-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-propyl}-benzo[1,3]dioxol-2-ylmethyl)-carbamic Acid Benzyl Ester

Product 1

HCID 22061562N-[2-(2-aminomethyl-benzo[1,3]dioxol-5-yl)-1-methyl-ethyl]-N-ethyl-2,2,2-trifluoro-acetamideYield 79.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 987 mg (2.1 mmol) of 2I was added 50 mL of anhydrous methanol followed by 150 mg of 10% Pd—C. This mixture was hydrogenated under atmospheric pressure 18 hours, filtered and the residue was washed with 50 mL of methanol. The combined filtrate was concentrated to dryness, and the residue was purified by silica gel column chromatography using 5% methanol in ethyl acetate to give 558 mg (1.67 mmol, 79%) of 2J as a colorless gum (M+H, 333).

Workup

  1. customwas hydrogenated under atmospheric pressure 18 hours
  2. filtrationfiltered
  3. washthe residue was washed with 50 mL of methanol
  4. concentrationThe combined filtrate was concentrated to dryness
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9501fe2bbebe42f4879b7a55715f3ce2
Source dataset
uspto-grants-2006_06
Patent number
US07060847B2

Reaction notes

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