Tert-butyl 2-[4-(dibenzylamino)cyclohexoxy]acetate → Tert-butyl 2-(4-aminocyclohexoxy)acetate

Participants

Reaction Steps

Tert-butyl 2-[4-(dibenzylamino)cyclohexoxy]acetate (6 g, 15 mmol, 1 eq.) was dissolved in methanol (200 mL) and pumped through the H-Cube® hydrogenation instrument containing a 10% Pd(OH)2 catalyst cartridge (CatCart) and using full hydrogen flow, ambient pressure, at 40° C. for 3 hours. The solvent was removed under vacuum to provide tert-butyl 2-(4-aminocyclohexoxy)acetate (3.3 g, 98%); (CI, m/z): [M+H]+ 230; 1H NMR (400 MHz, CDCl3): δ 3.99 (s, 2H), 3.31 (tt, J=10.7, 4.2 Hz, 1H), 2.71 (tt, J=10.8, 3.9 Hz, 1H), 2.00-2.11 (m, 2H), 1.83-1.93 (m, 2H), 1.46-1.51 (m, 9H), 1.29-1.44 (m, 4H), 1.06-1.19 (m, 2H).

Provenance & Evidence