9-Borabicyclo(3.3.1)nonane → 5-Hydroxy-3-(2-methyl-pyrimidin-5-yl)-pentanoic acid ethyl ester

HRID 1827680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827680
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[CH:7]=[CH2:8])[CH3:2].B1C2CCCC1CCC2.C([O-])(O)=[O:27].[Na+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[CH2:7][CH2:8][OH:27])[CH3:2]

Komponenten

5

Edukt 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 516892Sodium BicarbonateHCID 235812733-(2-Methyl-pyrimidin-5-yl)-pent-4-enoic acid ethyl ester

Produkt 1

HCID 235812815-Hydroxy-3-(2-methyl-pyrimidin-5-yl)-pentanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-4 (422 mg, 1.92 mmol) in THF was added 5.75 mL of 9-BBN (0.5 M/THF). After 18 hours, a slurry of NaBO3 (2.35 g) and NaHCO3 (2.42 g) in H20 (10 mL) was added and the mixture stirred vigorously for 1 hour. The mixture was extracted with CHCl3, washed with brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 3% EtOH/EtOAc) to give 4-5 as a clear oil.

Aufarbeitung

  1. extractionThe mixture was extracted with CHCl3
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customremoval of the solvent
  5. customthe residue was chromatographed (silica gel, 3% EtOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6494239def074b9dae0b4b18ce242276
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056909B2

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