3-[4-Hydroxy-2-(hydroxyimino-methyl)-phenyl]-acrylic acid tert-butyl ester → Tert-butyl-3-[2-(aminomethyl)-4-hydroxyphenyl]propanoate

HRID 1181039Notes

Reaction equation

HRID 1181039 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH:16]=[N:17]O)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH2:17])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 724795743-[4-Hydroxy-2-(hydroxyimino-methyl)-phenyl]-acrylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 17984622Tert-butyl-3-[2-(aminomethyl)-4-hydroxyphenyl]propanoateYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-[4-hydroxy-2-(hydroxyimino-methyl)-phenyl]-acrylic acid tert-butyl ester (0.50 g, 1.9 mmol) in ethanol (50 mL) was treated with 10% palladium on carbon (0.25 g). The resulting suspension was treated with hydrogen using a Parr shaker apparatus at ambient temperature and 50 psi for 16 h. The reaction mixture was filtered through Celite, rinsed with ethanol (20 mL), and concentrated. The residue was dissolved in ethyl acetate (50 mL) and washed with 10% K2CO3 solution (2×25 mL) and 1N NaOH (2×25 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was crystallized from isopropyl acetate to give the title compound (0.14 g, 40%), mp 154-157° C. 1H NMR (CD3OD): δ 1.37 (s, 9H), 2.44-2.50 (t, 2H), 2.80-2.85 (t, 2H), 3.75 (s, 2H), 4.83 (s, 3H), 6.57-6.63 (dd, 1H), 6.75-6.77 (d, 1H), 6.95-7.00 (d, 1H). MS (ES+) m/z 252.1 ([M+H]+). MS (ES−) m/z 250.2 ([M−H]−). Anal. Calculated for C14H21NO3: C: 66.9069; H: 8.4222; N: 5.5731. Found: C: 66.57; H: 8.29; N: 5.60.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washrinsed with ethanol (20 mL)
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  5. washwashed with 10% K2CO3 solution (2×25 mL) and 1N NaOH (2×25 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was crystallized from isopropyl acetate

Sources & evidence

ORD record
ord-a8d1c264d5fa4c359d7ac1516dcb0bf2
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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