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

HRID 546375Notes

Reaction equation

HRID 546375 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

Reactant 1

HCID 671891181-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)but-3-yn-1-ol

Product 1

HCID 671924741-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)butan-1-olYield 65.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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).

Workup

  1. customthe reaction was again flushed with nitrogen
  2. filtrationThe reaction was filtered through a pad of silica
  3. custompurified by silica chromatography

Sources & evidence

ORD record
ord-527172c2443947678f8de50ebf45042d
Source dataset
uspto-grants-2011_05
Patent number
US07935848B2

Reaction notes

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