Sodium borohydride → HCID 66817662, compound

HRID 1755063Notes

Reaction equation

HRID 1755063 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20]=[O:21])[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][OH:21])[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86672780HCID 86672780, compound

Product 1

HCID 66817662HCID 66817662, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (89 mg, 2.35 mmol) was added to a solution of 4-(2-oxo-ethyl)-cyclohexanecarboxylic acid benzyl ester (306 mg, 1.18 mmol) in methanol (6 ml) at 0° C. The mixture was stirred at 0° C. for one hour, and then quenched with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid benzyl ester (299 mg).

Workup

  1. customquenched with a saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0de2ec3414ad40e88c2454cb5b65c101
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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