Sodium Hydroxide → ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate

HRID 350781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350781
[CH2:1]([O:3][C:4]([N:6]1[CH2:22][CH2:21][C@@H:9]2[N:10]3[C:19]4[C:18]([C@@H:8]2[CH2:7]1)=[CH:17][CH:16]=[CH:15][C:14]=4[NH:13][C:12](=O)[CH2:11]3)=[O:5])[CH3:2].[OH-].[Na+]>Cl>[CH2:11]1[N:10]2[C@H:9]3[CH2:21][CH2:22][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][C@H:8]3[C:18]3[C:19]2=[C:14]([CH:15]=[CH:16][CH:17]=3)[NH:13][CH2:12]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 20578971ethyl (10R,15S)-3-oxo-1,4,12-triazatetracyclo[7.6.1.05,16.010,15]hexadeca-5,7,9(16)-triene-12-carboxylate

Produkt 1

HCID 86591143ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To ethyl-(6bR,10aS)-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.41 g, 14.6 mmol) was added 1M BH3 THF complex solution (36.6 mL). The reaction was heated under reflux for 5 hr. After the reaction cooled down to r.t, 6N HCl (40 mL) was added dropwise with chilling. The reaction solution was heated under reflux for 30 minutes. After cooled down to r.t., 1N NaOH was added to adjust the pH to 8. The reaction was extracted with CH2Cl2 (2×200 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated to afford ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.10 g, 98%). The product was used in next step without further purification. MS-APcI: 288 [MH]+

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 5 hr
  3. temperatureAfter the reaction cooled down
  4. temperaturewith chilling
  5. temperatureThe reaction solution was heated
  6. temperatureunder reflux for 30 minutes
  7. extractionThe reaction was extracted with CH2Cl2 (2×200 mL)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fb53185ad2094e69806e3966e74cf076
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183282B2

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