2-Benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-7-yl-acrylic acid methyl ester → 2-Amino-3-bicyclo[2.2.1]hept-7-yl-propionic acid methyl ester

HRID 19363Notes

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[CH:10]2[CH2:11][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[CH:10]2[CH2:9][CH2:8][CH:7]1[CH2:12][CH2:11]2

Participants

Conditions

Temperature: 25 °C

Procedure

In a flask was placed 2-benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-7-yl-acrylic acid methyl ester (130 mg, 0.40 mmol) and methanol (5 mL). To the mixture was added 10% palladium on activated carbon (15 mg) and the flask was fitted with a balloon filled with hydrogen. The mixture was allowed to stir at 25° C. for 1 h. After such time, the mixture was filtered through celite and concentrated in vacuo to afford crude 2-amino-3-bicyclo[2.2.1]hept-7-yl-propionic acid methyl ester (100 mg) which was used without purification.

Workup

customIn a flask was placed
customthe flask was fitted with a balloon
filtrationAfter such time, the mixture was filtered through celite and
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-337762ae267f457a9c3642fc5e77addc
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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