Sodium borohydride → 2-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-ol

HRID 1750472Notes

Reaction equation

HRID 1750472 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:19])([F:18])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:6]=1>C(O)C>[F:19][C:4]([F:3])([F:18])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[OH:17])[CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1183081902-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-one

Product 1

HCID 1183080552-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.117 g, 3.08 mmol) was added to a solution of 2-{[4-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-one (0.375 g, 1.54 mmol) in ethanol (10 ml). The reaction was stirred at room temperature for 3 hours and then quenched with water (5 mL) and 2M HCl (aq., 5 ml). The organics were extracted with ethyl acetate (2×30 ml) and the combined organics were washed with brine (10 ml), dried over magnesium sulfate, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-35% ethyl acetate/petrol) to afford the title compound as two diastereomers.

Workup

  1. customquenched with water (5 mL) and 2M HCl (aq., 5 ml)
  2. extractionThe organics were extracted with ethyl acetate (2×30 ml)
  3. washthe combined organics were washed with brine (10 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through a hydrophobic frit
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica, 0-35% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-363dce2a403240dda67b6d4d185ea39d
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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