4-Aminopyridine → HCID 11052254, compound

HRID 854145Notes

Reaction equation

HRID 854145 reaction equation
N[C:2]1[CH:7]=CN=C[CH:3]=1.[CH2:8]([C@H:10]1[O:12][CH2:11]1)[Cl:9].[C]=[O:14].[CH:15]([OH:18])(C)C>>[CH:2]([O:14][C:15](=[O:18])[CH2:11][C@H:10]([OH:12])[CH2:8][Cl:9])([CH3:7])[CH3:3]

Participants

5

Reactant 4

HCID 17274-AminopyridineHCID 3776IsopropanolHCID 149428(+)-EpichlorohydrinHCID 178418416HCID 178418416, compound

Product 1

HCID 11052254HCID 11052254, compoundYield 80%

Procedure

In a 50 mL-volumeric autoclave were added deaerated isopropanol (20 mL), 4-aminopyridine 47 mg (0.5 mmol) and (S)-epichlorohydrin (1.9 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 (1.5 MPa) was introduced therein and the mixture was reacted at 40° C. for 25 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-chloro-3-hydroxybutanoic acid isopropyl ester (2.7 g, 80%, >99% ee) as a colorless oil.

Workup

  1. additionwas introduced
  2. customthe mixture was reacted at 40° C. for 25 hours
  3. customthe solvent was removed in vacuo
  4. distillationThe residue was subjected to Kugelrohr distillation

Sources & evidence

ORD record
ord-2afbe10ca0a8425f9499df0bd1aebf72
Source dataset
uspto-grants-2007_08
Patent number
US07256305B2

Reaction notes

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