ethyl (2S*,3R*)-2-(dibenzylamino)-3-hydroxy-4,4-dimethyl-pentanoate → ethyl (2S*,3R*)-2-amino-3-hydroxy-4,4-dimethyl-pentanoate

HRID 530575Notes

Reaction equation

HRID 530575 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]([C@H:15]([OH:20])[C:16]([CH3:19])([CH3:18])[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:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 1

HCID 86700027ethyl (2S*,3R*)-2-(dibenzylamino)-3-hydroxy-4,4-dimethyl-pentanoate

Product 1

HCID 86700026ethyl (2S*,3R*)-2-amino-3-hydroxy-4,4-dimethyl-pentanoateYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a pear flask, at rt, ethyl (2S*,3R*)-2-(dibenzylamino)-3-hydroxy-4,4-dimethyl-pentanoate (2.0 g, 5.6 mmol) was dissolved in EtOH (110 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 (0.74 g, 70%) was obtained as yellowish oil and used without further purification in the following step. MS (ESI) m/z: 190 [M−H]+. 1H NMR (DMSO-d6) δ 0.90 (s, 9H), 1.20 (t, J=7.11 Hz, 3H), 3.35 (d, J=2.95 Hz, 1H), 3.44 (d, J=2.92 Hz, 1H), 4.05-4.13 (m, 2H).

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-4e30733035c34913b56c657b47df27dd
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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