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Methanol → (R)-6-Benzyloxy-1-(2-hydroxypropyl)-3-aminoindazole

HRID 1715728
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1715728
[N:1](OC(C)(C)C)=O.[CH2:8]([O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([NH:24][CH2:25][C@H:26]([OH:28])[CH3:27])[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO.C([O-])(=O)C.[NH4+]>O1CCCC1.[Zn].C(OCC)(=O)C>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:19]([C:20]([NH2:1])=[N:21][N:24]2[CH2:25][C@H:26]([OH:28])[CH3:27])=[CH:22][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 887MethanolHCID 10906Tert-Butyl nitriteHCID 517165Ammonium AcetateHCID 11858494HCID 11858494, Verbindung

Produkt 1

HCID 11635595(R)-6-Benzyloxy-1-(2-hydroxypropyl)-3-aminoindazoleAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994
Zinc
Katalysator
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

Tert-butyl nitrite (759 mL, 6.38 mol) was added to a stirred solution of (R)-4-benzyloxy-2-(2-hydroxypropyl)aminobenzonitrile (1), prepared according to the methods described in WO 02/98861 A1 and WO 02/98862 A1 (1.20 kg, 4.25 mol) in 12 L of tetrahydrofuran under an atmosphere of nitrogen. After 1 h, the solution was cooled to 15° C., and 2.6 L of methanol was added followed by 10 L of saturated aqueous ammonium acetate solution. Zinc dust (1.1 kg, 17 mol) was added over 1.5 h, keeping the reaction temperature below 40° C. Ethyl acetate (10 L) was added, and the liquid phase was decanted from the solid residue and combined with that from one additional run on the same scale. The combined liquid phases were partitioned between ethyl acetate and brine. The organic solution was dried (Na2SO4), treated with decolorizing charcoal, filtered and concentrated in vacuo to afford 1976 g (78%) of 2.

Aufarbeitung

  1. customprepared
  2. customthe reaction temperature below 40° C
  3. customthe liquid phase was decanted from the solid residue
  4. customThe combined liquid phases were partitioned between ethyl acetate and brine
  5. dry with materialThe organic solution was dried (Na2SO4)
  6. additiontreated with decolorizing charcoal
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eb7cb87513ee44bc922644e84afdbfb6
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07799930B2

Notizen zur Reaktion

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