5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(1-hydroxy-cyclopentylethynyl)-nicotinamide → 5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-[2-(1-hydroxy-cyclopentyl)-ethyl]-nicotinamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:24]#[C:25][C:26]3([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])=[CH:4][CH:3]=1>C(OC(=O)C)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([CH2:24][CH2:25][C:26]3([OH:31])[CH2:27][CH2:28][CH2:29][CH2:30]3)=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])=[CH:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(1-hydroxy-cyclopentylethynyl)-nicotinamide (120 mg, 0.27 mmol) was dissolved in ethylacetate (15 mL) and hydrogenated in the presence of palladium on charcoal (10%) at room temperature and atmospheric pressure. After filtration and evaporation of the solvent the residue was purified by chromatography on silica gel with a ethyl acetate: methanol gradient to yield the product as colorless foam, MS (ISP) 443.1, 445.1 (M+H)+.