Sodium ethoxide → HCID 131732025, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C@H:8]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3][CH:2]=1.[O-]CC.[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][C@H:8]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3][CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To an ethanol solution (0.4 M) of cis-1-(1,1-dimethylethyl) 3-ethyl 4-(4-pyridinyl)-1,3-piperidinedicarboxylate (1 eq.) from the previous step was added freshly prepared sodium ethoxide (1.1 eq.). The resulting yellow-orange solution was heated at 60° C. for 12 h. The volatiles were then removed in vacuo and the residue was partitioned between EtOAc and sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4, treated with activated charcoal, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 80:20 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a pale yellow oil.