Hydrochloric Acid → methyl 3-(3-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate

HRID 1471757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471757
[Si]([O:8][CH2:9][C:10]1[C:11]([C:16]2[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[N:17]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.Cl>CO>[OH:8][CH2:9][C:10]1[C:11]([C:16]2[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[N:17]=2)=[N:12][CH:13]=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86690794methyl 3-(3-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate

Produkt 1

HCID 86690795methyl 3-(3-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To methyl 3-(3-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate in MeOH (10 mL) was added HCl (2 N, 1.2 mL, 10 eq.). The mixture was stirred at rt for 4 h, concentrated, neutralized to pH 7-8 with NaHCO3(sat) solution, and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, concentrated, and purified on silica gel using EtOAc as eluent to give methyl 3-(3-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate (51 mg, 67%) as an oil. LRMS (M+H+) m/z 262.1.

Aufarbeitung

  1. concentrationconcentrated
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-46eaac205c0648c0bff04310210b8d8d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012450B2

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