methyl (2R,3S)-3-azido-2-hydroxy-3-phenylpropanoate → (2R,3S)-3-Phenylisoserine methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([OH:15])[C@@H:5]([N:12]=[N+]=[N-])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:16])[C@H:4]([OH:15])[C@H:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH2:12]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The (2R,3S)-3-azido-2-hydroxy-3-phenylpropionic acid methyl ester (1, 0.5 g) is hydrogenated over 10% palladium on carbon (0.1 g) in ethanol at atmospheric pressure for 1 hour. The reaction is filtered and evaporated to yield the desired amine. Mp 106-108° C.
Workup
- filtrationThe reaction is filtered
- customevaporated
Sources & evidence
- ORD record
- ord-c8b78cf64d0541bd964e330cef865d22
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05965739
Reaction notes
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