ethyl (2S*,3R*)-2-(dibenzylamino)-3-hydroxy-pentanoate → ethyl (2S*,3R*)-2-amino-3-hydroxy-pentanoate

HRID 530551Notes

Reaction equation

HRID 530551 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]([C@H:15]([OH:18])[CH2:16][CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])C1C=CC=CC=1>CCO.[Pd]>[NH2:8][C@@H:9]([C@H:15]([OH:18])[CH2:16][CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 1

HCID 86699993ethyl (2S*,3R*)-2-(dibenzylamino)-3-hydroxy-pentanoate

Product 1

HCID 58287050ethyl (2S*,3R*)-2-amino-3-hydroxy-pentanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a pear flask, at rt, ethyl (2S*,3R*)-2-(dibenzylamino)-3-hydroxy-pentanoate (0.165 g, 0.48 mmol) was dissolved in EtOH (12 mL) and passed through the H-Cube® hydrogenator flow reactor, using 10% Pd/C as catalyst [flow:1.0 mL/min; P=1.0 bar, T=70° C.]. After evaporation of the solvent, the title compound was obtained as yellowish oil and used without further purification in the following step. MS (ESI) m/z: 162 [M−H]+.

Workup

  1. custom[flow:1.0 mL/min; P=1.0 bar, T=70° C.]
  2. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-bd4bb104d3d24c4a875464214ebe46ba
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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