Ammonium formate → (R)-8-fluoro-5-methoxy-3-aminochroman

HRID 52260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52260
C([N:8]([C@@H:16]1[CH2:21][C:20]2[C:22]([O:27][CH3:28])=[CH:23][CH:24]=[C:25]([F:26])[C:19]=2[O:18][CH2:17]1)CC1C=CC=CC=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.C1COCC1.[Pd]>[NH2:8][C@@H:16]1[CH2:21][C:20]2[C:22]([O:27][CH3:28])=[CH:23][CH:24]=[C:25]([F:26])[C:19]=2[O:18][CH2:17]1

Komponenten

6

Edukt 2

HCID 2723923Ammonium formateHCID 20640362(R)-3-(N,N-Dibenzylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

Produkt 1

HCID 22871215(R)-8-fluoro-5-methoxy-3-aminochromanAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

(R)-3-(N,N-Dibenzylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (13.0 g, 34.4 mmol) was dissolved in 265 mL methanol and 115 mL THF. To this was 10% Pd/C (4 g) and ammonium formate (51.5 g, 0.817 mol) added. The reaction was heated to 50° C. for 2.5 h. The reaction was filtered and the solvent was removed in vacuo, the remains were taken into a 2 M solution of NaOH and then extracted twice with ether. The combined ether portions were treated with brine, dried (Na2SO4), filtered, and the solvent removed in vacuo to give 6.2 g (91% yield) of the title compound as a clear oil. [α]21D =-15.3° (C=1 CHCl3) GC-MS (70 eV) M=197 (51%).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed in vacuo
  3. extractionextracted twice with ether
  4. additionThe combined ether portions were treated with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5873e019fbd4454a97065d1d92f5c096
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616610

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