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

HRID 989044ノート

反応式

HRID 989044 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-f47ee08521574119944deeb07dbcdd24
出典データセット
uspto-grants-2003_10
特許番号
US06638934B2

反応ノート

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