Methanol → 9-Chloro-3-carbobenzyloxy-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoxaline

HRID 989044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989044
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=O)[CH:8]3[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:17])[CH2:13][CH2:12][N:9]32)=[CH:4][CH:3]=1.B.C1COCC1.CO>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][CH2:7][CH:8]3[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[O:17])[CH2:13][CH2:12][N:9]32)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 121094739-chloro-3-carbobenzyloxy-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one

Produkt 1

HCID 121094749-Chloro-3-carbobenzyloxy-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoxalineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 9-chloro-3-carbobenzyloxy-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a ]-quinoxalin-5(6H)-one (1.45 g, 3.9 mmol) in 50 ml THF was added a solution of borane-THF complex (1M in THF, 12.2 ml, 12.2 mmol). After 15 min, the reaction was heated to reflux. After MS showed the absence of starting material, the reaction mixture was cooled to rt. Methanol was added and the solution concentrated to a yellow residue. This was repeated and the crude material was purified by column chromatography using a Biotage© Flash 40i (4.0×15.0 cm column, load with methylene chloride, elute with 25-30% ethyl acetate/hexanes) to give 9-Chloro-3-carbobenzyloxy-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoxaline as an off-white solid (898.3 mg, 65%). 1H NMR (CDCl3, 300 MHz) δ7.32-7.38 (m, 5H), 6.56-6.66 (m, 2H), 6.37-6.40 (m, 1H), 5.16 (s, 2H), 4.19 (m, 2H), 3.61-3.71 (m, 2H), 3.33-3.36 (m, 1H), 3.05-3.23 (m, 2H), 2.72-2.79 (m, 2H) ppm. MS (ESI) m/z=358 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction was heated to reflux
  2. concentrationthe solution concentrated to a yellow residue
  3. customthe crude material was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f47ee08521574119944deeb07dbcdd24
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638934B2

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