2-Benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-2-yl-acrylic acid methyl ester → 2-Amino-3-bicyclo[2.2.1]hept-2-yl-propionic acid methyl ester

HRID 19354Notes

Reaction equation

HRID 19354 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([NH:13]C(OCC1C=CC=CC=1)=O)=[CH:5][CH:6]1[CH2:11][CH:10]2[CH2:12][CH:7]1[CH2:8][CH2:9]2.[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:24])[CH:4]([NH2:13])[CH2:5][CH:6]1[CH2:11][CH:10]2[CH2:12][CH:7]1[CH2:8][CH2:9]2

Participants

5

Reactant 2

HCID 668955732-Benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-2-yl-acrylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 142814412-Amino-3-bicyclo[2.2.1]hept-2-yl-propionic acid methyl esterYield 70.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

In a flask was placed 2-benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-2-yl-acrylic acid methyl ester (491 mg, 1.49 mmol) and methanol (15 mL). To this mixture added 10% palladium on activated carbon (60 mg) and the flask was fitted with a balloon filled with hydrogen. The mixture was allowed to stir at 25° C. for 1 h and then filtered through celite and concentrated in vacuo to afford 2-amino-3-bicyclo[2.2.1]hept-2-yl-propionic acid methyl ester (206 mg, 70%) as a white solid.

Workup

  1. customIn a flask was placed
  2. customthe flask was fitted with a balloon
  3. filtrationfiltered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19cf7c373cac4120b495b62bacc76c44
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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