4-Aminopyridine → HCID 86605369, compound

HRID 854144Notes

Reaction equation

HRID 854144 reaction equation
NC1C=CN=CC=1.[O:8]1[C@@H:10]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9]1.[C]=O.[H][H].[C:19]([O:22][CH2:23][CH3:24])(=[O:21])C>C(O)C>[CH2:23]([O:22][C:19](=[O:21])[CH2:9][C@@H:10]([OH:8])[CH2:11][CH2:12][CH2:13][CH3:14])[CH3:24]

Participants

7

Reactant 5

HCID 17274-AminopyridineHCID 8857Ethyl AcetateHCID 1549991(2S)-2-butyloxiraneHCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 86605369HCID 86605369, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50 mL-volumetric autoclave were added deaerated ethanol (10 mL) and ethyl acetate (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-1,2-epoxyhexane (2.0 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) and hydrogen gas (1 MPa) were introduced therein and the mixture was reacted at 35° C. for 28 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-3-hydroxyheptanoic acid ethyl ester (2.92 g, 85%, >99% ee) as a colorless oil.

Workup

  1. additionwere introduced
  2. customthe mixture was reacted at 35° C. for 28 hours
  3. customthe solvent was removed in vacuo
  4. distillationThe residue was subjected to Kugelrohr distillation

Sources & evidence

ORD record
ord-ae50dea6e51241bc8778130daca9d8e9
Source dataset
uspto-grants-2007_08
Patent number
US07256305B2

Reaction notes

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