HCID 58906458, compound → Tert-butyl 4-methoxy-4-((methylamino)methyl)piperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:16][N:17](CC2C=CC=CC=2)[CH3:18])([O:14][CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([O:14][CH3:15])([CH2:16][NH:17][CH3:18])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Amine (36) (55 g, 158 mmol) was dissolved in ethyl acetate (500 ml). Pd—C (10%, wet, 5 g) was added and the mixture was stirred for 23 h under hydrogen atmosphere (1 bar). TLC analysis revealed incomplete conversion. Extra Pd—C (2.5 g) was added and the mixture was stirred under H2 (1 bar) for 110 h. NMR analysis revealed complete conversion. The mixture was filtrated over Celite, the Celite crop was washed with ethyl acetate and the filtrate was evaporated to dryness. The residue was purified by distillation (bulb to bulb, 0.04 mbar, 130° C.) giving 35 g of compound (37) (86%) as colorless oil.