ethyl (2S*,3R*)-2-(dibenzylamino)-3-hydroxy-4-methyl-pentanoate → ethyl (2S*,3R*)-2-amino-3-hydroxy-4-methyl-pentanoate
Reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]([C@H:15]([OH:19])[CH:16]([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:19])[CH:16]([CH3:18])[CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In a pear flask, at rt, ethyl (2S*,3R*)-2-(dibenzylamino)-3-hydroxy-4-methyl-pentanoate (1.24 g, 3.5 mmol) was dissolved in EtOH (75 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 (0.57 g, quant.) was obtained as yellowish oil and used without further purification in the following step. MS (ESI) m/z: 176 [M−H]+. 1H NMR (DMSO-d6) δ 0.83 (d, J=6.72 Hz, 3H), 0.90 (d, J=6.69 Hz, 3H), 1.19 (t, J=7.10 Hz, 3H), 1.64-1.80 (m, 1H), 3.29 (dd, J=3.36, 8.06 Hz, 1H), 3.35 (d, J=3.37 Hz, 1H), 4.08 (qd, J=0.99, 7.13 Hz, 2H).