Methanol → HCID 11984349, compound

HRID 854146Notes

Reaction equation

HRID 854146 reaction equation
C[OH:2].NC1C=CN=CC=1.[CH2:10]([O:17][CH2:18][C@@H:19]1[O:21][CH2:20]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C]=O.C1[CH2:28][O:27][CH2:26]C1>>[CH3:26][O:27][C:28](=[O:2])[CH2:20][C@@H:19]([OH:21])[CH2:18][O:17][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 17274-AminopyridineHCID 8028TetrahydrofuranHCID 159746(-)-Benzyl (R)-glycidyl etherHCID 178418416HCID 178418416, compound

Product 1

HCID 11984349HCID 11984349, compoundYield 89%

Procedure

In a 50 mL-volumetric autoclave were added deaerated methanol (15 mL) and THF (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (R)-benzylglycidyl ether (3.3 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) was introduced therein and the mixture was reacted at 35° C. for 24 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (R)-4-benzyloxy-3-hydroxybutanoic acid methyl ester (4.0 g, 89%, >99% ee) as a colorless oil.

Workup

  1. additionwas introduced
  2. customthe mixture was reacted at 35° C. for 24 hours
  3. customthe solvent was removed in vacuo
  4. distillationThe residue was subjected to Kugelrohr distillation

Sources & evidence

ORD record
ord-d9ee2611a8244b43a00796b90b0c1d76
Source dataset
uspto-grants-2007_08
Patent number
US07256305B2

Reaction notes

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