methyl (2R,3S)-3-azido-2-hydroxy-3-phenylpropanoate → (2R,3S)-3-Phenylisoserine methyl ester

HRID 1072939Notes

Reaction equation

HRID 1072939 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

HCID 10059351methyl (2R,3S)-3-azido-2-hydroxy-3-phenylpropanoate

Product 1

HCID 10176516(2R,3S)-3-Phenylisoserine methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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

  1. filtrationThe reaction is filtered
  2. customevaporated

Sources & evidence

ORD record
ord-f47ce68773b044deaa2fb83f55e55f98
Source dataset
uspto-grants-2005_06
Patent number
US06911549B1

Reaction notes

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