Water → 3-amino-7-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-on

HRID 1033385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033385
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:16])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 538629013-Azido-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Produkt 1

HCID 544585903-amino-7-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-onAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Azido-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (3.36 g, 15.3 mmol) (Step C) dissolved in dry tetrahydrofuran was treated with 4.00 g (15.3 mmol; leq) of triphenylphosphine and the resulting solution stirred at room temperature under nitrogen for 2 hours. Water (0.48 mL, 2eq) was added and the mixtured stirred at room temperature for 16 hours. Solvents were removed under vacuum and the residue purified by preparative HPLC on silica, eluting with methylene chloride/methanol (9:1) to afford 2.39 g (12.3 mmol, 81%) of product. 1H NMR (200MHz, CD3OD): 1.87 (m,1H), 2.41 (m,1H), 2.6-2.9 (m,2H), 3.30 (dd;8,12 Hz;1H), 7.0 (m,3H). FAB-MS: calculated for C10H11FN2O 194; found 195 (M+H,100%).

Aufarbeitung

  1. stirringthe mixtured stirred at room temperature for 16 hours
  2. customSolvents were removed under vacuum
  3. customthe residue purified by preparative HPLC on silica
  4. washeluting with methylene chloride/methanol (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-4fd1a3a423fe4118a6498ff14dfc08c2
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310737

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