Methyl 2-(8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-yl)acetate → 1,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-one
Reaction equation
[N+:1]([CH2:4][C:5]1([CH2:15][C:16]([O:18]C)=O)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)([O-])=O>CO.[Pd]>[O:12]1[C:8]2([CH2:13][CH2:14][C:5]3([CH2:15][C:16](=[O:18])[NH:1][CH2:4]3)[CH2:6][CH2:7]2)[O:9][CH2:10][CH2:11]1Participants
4
Procedure
To a slurry of Methyl [8-(nitromethyl)-1,4-dioxaspiro[4.5]dec-8-yl]acetate (1 g, 4.7 mmol) in Methanol (20 mL) was added Pd/C (1 g, 10%) under N2 atmosphere. The reaction mixture was stirred at room temperature under 5 kg/cm2 H2 pressure for 12 h. After completion, the reaction mixture was filtered through celite pad, washed with methanol and the filtrate was concentrated under reduced pressure to afford the title compound as a white solid (0.7 g, 70%). 1H NMR (400 MHz, DMSO-d6) δ 7.46 (s, 1H), 3.83 (s, 4H), 3.00 (s, 2H), 2.00 (s, 2H), 1.56-1.51 (m, 8H).