Water → HCID 66734557, Verbindung

HRID 1963262

Reaktionsgleichung

Reaktionsgleichung von HRID 1963262
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][C:17]([CH3:23])([CH3:22])[CH2:18][CH2:19][Mg]Cl.[C:24](Cl)(=[O:27])[O:25][CH3:26].O>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][N:13]([C:24]([O:25][CH3:26])=[O:27])[CH:14]([CH2:19][CH2:18][C:17]([CH3:23])([CH3:22])[CH3:16])[CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 109878804-({[tert-Butyl(dimethyl)silyl]oxy}methyl)pyridine2×HCID 178444610HCID 178444610, Verbindung

Produkt 1

HCID 66734557HCID 66734557, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

4-((tert-Butyldimethylsilyloxy)methyl)pyridine (5.58 g, 25 mmol) (from reference compound 4, step 1) was dissolved in dry THF (50 mL) under nitrogen and the mixture cooled to −15° C. (3,3-Dimethylbutyl)magnesium chloride (0.5 M in THF) (50 mL, 25 mmol) was added dropwise during 20 min to yield a yellow solution which was stirred at −15° C. for 30 min. Then, methyl carbonochloridate (2.5 mL, 32 mmol) was added during 1 min. The reaction was continued at −15° C. for 30 min and then the mixture was cooled to −60° C. After 2 h the temperature had reached room temperature. Water (20 mL) was added and the solvent evaporated. The aqueous phase was extracted with DCM (×2) and the combined organic phase passed through a phase separator. The solvent was evaporated to yield a yellow oil. The residue was purified via Biotage (0=>10% EtOAc in heptane) to yield methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)pyridine-1(2H)-carboxylate (3.67 g, 44%) as a colourless oil. MS m/z 368 (M+H)+

Aufarbeitung

  1. additionwas added dropwise during 20 min
  2. customto yield a yellow solution which
  3. waitThe reaction was continued at −15° C. for 30 min
  4. temperaturethe mixture was cooled to −60° C
  5. waitAfter 2 h the temperature had reached room temperature
  6. customthe solvent evaporated
  7. extractionThe aqueous phase was extracted with DCM (×2)
  8. customThe solvent was evaporated
  9. customto yield a yellow oil
  10. customThe residue was purified via Biotage (0=>10% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-ba419a0ec0f34ddea094a44b8fe3fdbd
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415378B2

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