8-(4-Nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane → 4-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)aniline

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Reaction Steps

A mixture of 8-(4-nitro-phenyl)-1,4-dioxa-8-aza-spiro[4.5]decane (Synthesis, 606, 1981) (3.5 g, 13.3 mmol) and 10% Pd/C (0.5 g) in 100 mL of ethanol/methylene chloride(2:1) was pressurized with 30 psi hydrogen and shaken over 1 hours. The catalyst was then removed by filtering through a short pad of silica gel to give the title compound (2.8g, 90%) as a grey solid; 1H NMR (300 MHz, DMSO-d6) δ 1.85-2.00 (m, 4H), 3.00-3.10 (m, 4H), 3.93 (s, 4H), 6.60 (d, J=6.0 Hz, 2H), 6.80 (d, J=6.0 Hz, 2H); MS (ES) m/z: 235.2 (MH+); HRMS Calcd. for C13H18N2O2: 234.1380. Found: 234.1371.

Provenance & Evidence