Formic Acid → 1374243-36-3

Reaction equation

[CH2:1]([N:8](C)[CH:9]1[CH2:15][O:14][CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10]1)C1C=CC=CC=1.C(O)=O>CO.[Pd]>[CH3:1][NH:8][CH:9]1[CH2:15][O:14][CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10]1

Participants

Procedure

A solution of tert-butyl 6-(benzyl(methyl)amino)-1,4-oxazepane-4-carboxylate (0.795 g (2.48 mmol) 107.2 in MeOH (20 mL) was treated with 5% Pd/C (0.26 g) and HCO2H (1 mL). The black suspension was stirred under a 60 PSI H2 atmosphere for 22 hr. The catalyst was removed by filtration through celite and the filtrate was concentrated in vacuo to remove volatiles. The residue was diluted with EtOAc and washed with sat′d NaHCO3, dried over MgSO4, filtered, and concentrated to yield 0.tert-butyl 6-(methylamino)-1,4-oxazepane-4-carboxylate (0.17 g) 107.3 as a clear viscous oil that was used without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.82-3.60 (m, 5H), 3.59-3.48 (m, 1H), 3.47-3.33 (m, 3H), 3.26 (dd, J=6.5, 14.6 Hz, 1H), 2.93-2.82 (m, 2H), 2.46 (s, 3H), 1.48 (s, 9H); LCMS (ESI) m/z: 231.10 [M+H]−.