Ethanol → tert-Butyl [(3S,5R)-1-(5-amino-2,3-dihydrofuro[2,3-b]pyridin-4-yl)-5-(trifluoromethyl)piperidin-3-yl]carbamate

HRID 1499507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499507
[N+:1]([C:4]1[C:5]([N:13]2[CH2:18][C@H:17]([C:19]([F:22])([F:21])[F:20])[CH2:16][C@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:14]2)=[C:6]2[CH2:12][CH2:11][O:10][C:7]2=[N:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].CCO>[Fe].O>[NH2:1][C:4]1[C:5]([N:13]2[CH2:18][C@H:17]([C:19]([F:22])([F:20])[F:21])[CH2:16][C@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:14]2)=[C:6]2[CH2:12][CH2:11][O:10][C:7]2=[N:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 86726737HCID 86726737, Verbindung

Produkt 1

HCID 86726738tert-Butyl [(3S,5R)-1-(5-amino-2,3-dihydrofuro[2,3-b]pyridin-4-yl)-5-(trifluoromethyl)piperidin-3-yl]carbamateAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of tert-butyl [(3S,5R)-1-(5-nitro-2,3-dihydrofuro[2,3-b]pyridin-4-yl)-5-(trifluoromethyl)piperidin-3-yl]carbamate (227.1 mg, 0.5252 mmol), iron powder (289.6 mg, 5.186 mmol) and ammonium chloride (462.4 mg, 8.644 mmol) was added EtOH (5.0 mL) followed by water (2.5 mL). The mixture was stirred at 80° C. for 1 h. The reaction mixture was filtered through a pad of diatomaceous earth. The diatomaceous earth pad was eluted with a 10% aqueous solution of K3PO4 (50 mL), and EtOAc (50 mL). The separated organic layer was washed with brine (50 mL), dried over Na2SO4, and concentrated to give the crude sub-title compound (211.5 mg). The crude product was used directly in the next step without further purification. LCMS calc. for C18H26F3N4O3 (M+H)+: m/z=403.2. found 403.2.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washThe diatomaceous earth pad was eluted with a 10% aqueous solution of K3PO4 (50 mL), and EtOAc (50 mL)
  3. washThe separated organic layer was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e507af0df978425da03de9f85dcdc679
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200004B2

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