{4-[4-((2R)-2,3-Dihydroxypropylamino)phenyl]butyl}carbamic acid benzyl ester → 4-[4-((2R)-2,3-Dihydroxypropylamino)phenyl]butylamine

Participants

Reaction Steps

The protected amine 700 (0.29 g, 0.77 mmol) was stirred at room temperature for 6 h in methanol (20 mL) with 10% Pd/C (129 mg, 50% wet) under hydrogen (1 atm). The catalyst was filtered off and the solvent was removed under reduced pressure to give amine 710 (0.165 g, 90%) as a clear oil. 1H NMR (300 MHz, CD3OD) δ 1.56 (m, 4H), 2.51 (t, 2H), 2.71 (t, 2H), 3.02 (m, 1H), 3.27 (m, 1H), 3.30 (m, 2H), 3.56 (m, 2H), 3.80 (m, 1H), 6.60 (d, 2H), 6.95 (d, 2H). m/z (ESI) 239 [C13H22N2O2+H]+.

Provenance & Evidence