Hydrazine → ((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone

HRID 1747155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747155
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][N:9]([C:12]([C@:14]34[CH2:21][C@H:20]([N:22]5C(=O)C6C(=CC=CC=6)C5=O)[CH2:19][C@H:15]3[O:16][CH2:17][CH2:18]4)=[O:13])[CH2:8][C:7]=2[CH:33]=1.NN>C(O)C>[NH2:22][C@@H:20]1[CH2:19][C@H:15]2[O:16][CH2:17][CH2:18][C@@:14]2([C:12]([N:9]2[CH2:8][C:7]3[CH:33]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:4]=[CH:5][C:6]=3[O:11][CH2:10]2)=[O:13])[CH2:21]1

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 867081552-((3aS,5S,6aR)-3a-(6-(trifluoromethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine-3-carbonyl)hexahydro-2H-cyclopenta[b]furan-5-yl)isoindoline-1,3-dione

Produkt 1

HCID 86708156((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of the product of Step D (5.39 g, 11.1 mmol, 1 eq) and hydrazine (7.1 mL, 222 mmol, 20 eq) in ethanol (60 mL) was stirred at rt 18 hours. The white solid was filtered, washed with methanol and DCM, and the filtrates concentrated. Saturated NaHCO3 was added, the aqueous extracted with DCM, the organics combined, dried over MgSO4 and concentrated to afford the product of Step E. Calculated for C17H19F3N2O3: 357.1 (M+1). found: 357.3.

Aufarbeitung

  1. filtrationThe white solid was filtered
  2. washwashed with methanol and DCM
  3. concentrationthe filtrates concentrated
  4. additionSaturated NaHCO3 was added
  5. extractionthe aqueous extracted with DCM
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aaf9f4cce2fe425cb21e4075fdf669df
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150532B2

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