HCID 54224654, compound → HCID 53658627, compound

HRID 2260387Notes

Reaction equation

HRID 2260387 reaction equation
[N:1]([C@@H:4]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[C@@H:5]([OH:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[NH2:1][C@@H:4]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[C@@H:5]([OH:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 54224654HCID 54224654, compound

Product 1

HCID 53658627HCID 53658627, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.115 g of carbon powder carrying 10% of palladium is added to a solution of 1.15 g of ethyl (2R,3S)-3-azido-2-hydroxy-3-(4-methylphenyl)propionate in 35 cm3 of ethyl acetate. The reaction mixture is stirred under a hydrogen pressure of 120 kPa and at a temperature in the region of 22° C. for 8 hours and then filtered through sintered glass lined with Celite. The sintered glass is washed with 5 cm3 of ethyl acetate and the filtrates are combined and then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. 0.83 g of ethyl (2R,3S)-3-amino-2-hydroxy-3-(4-methylphenyl)propionate is thereby obtained in the form of a pale yellow paste.

Workup

  1. filtrationfiltered through sintered glass
  2. washThe sintered glass is washed with 5 cm3 of ethyl acetate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-b448b9dc366448f69d474bf82fa5fac4
Source dataset
uspto-grants-1995_12
Patent number
US05476954

Reaction notes

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