Sodium borohydride → 2-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-ol

HRID 1750478Notes

Reaction equation

HRID 1750478 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:19])([F:18])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])=[N:9][CH:10]=1>C(O)C>[F:18][C:4]([F:3])([F:19])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[OH:17])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1183081882-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-one

Product 1

HCID 1183080932-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.036 g, 0.954 mmol) was added to a solution of 2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-one (0.116 g, 0.48 mmol) in ethanol (5 ml). The reaction was stirred at room temperature for 1 hour and then quenched with water (5 ml) and 2M HCl (aq, 5 ml), basified with 2M NaOH (aq) and extracted with ethyl acetate (2×30 ml). The combined organics were dried over dried over magnesium sulfate, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-30% 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. extractionextracted with ethyl acetate (2×30 ml)
  3. customThe combined organics were dried
  4. dry with materialover dried over magnesium sulfate
  5. filtrationfiltered through a hydrophobic frit
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica, 0-30% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-d403c409b52d4d578cfb52ab6ba09343
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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