1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)but-3-yn-1-ol → 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)butan-1-ol
Reaction equation
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:21])[CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:21])[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:2])[CH3:3]Participants
4
Procedure
A solution of 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)but-3-yn-1-ol (286 mg, 1.00 mmol) in ethanol (6.0 mL) was flushed with nitrogen. Palladium on carbon (10%, 100 mg) was added and the reaction was again flushed with nitrogen. The reaction was then stirred at room temperature under an atmosphere of hydrogen overnight. The reaction was filtered through a pad of silica and purified by silica chromatography to give the desired hydrogenation product (190 mg).