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

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Reaction Steps

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).

Provenance & Evidence