Sodium borohydride → HCID 178520751, compound

HRID 516872Notes

Reaction equation

HRID 516872 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58069819Benzyl 2-(4-oxocyclohexyl)acetate

Product 1

HCID 178520751HCID 178520751, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl 2-(4-oxocyclohexyl)acetate (5.0 g, 20.3 mmol) was dissolved in methanol (150 ml), NaBH4 (770 mg, 20.3 mmol) was added by portions to the solution at 0° C., and the mixture was stirred for 2 hr. The mixture was concentrated under reduced pressure, followed by separation with ethyl acetate and water. The organic layer was washed with saturated brine and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=85:15) to give the title compound as an oil (900 mg, yield 18%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customfollowed by separation with ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-ada0855dd3a948eb81197ffce79086b2
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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