propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate → Propyl (7-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

HRID 476226

反応式

HRID 476226 の反応式
[N+](=[CH:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[NH:8][C:9]2[C:14]([C:15]=1[CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N-]>C([O-])(=O)CCCCCCC.[Rh+2].C([O-])(=O)CCCCCCC.C(Cl)Cl>[O:23]=[C:4]1[CH2:3][N:8]2[C:9]3[C:14]([C:15]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[C:7]2[CH2:6][CH2:5]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

参加物

4

反応物 1

HCID 86655415propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate

生成物 1

HCID 58399159Propyl (7-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate収率 64%

試薬・触媒・溶媒 2

HCID 10178397Rhodium(II) octanoate触媒HCID 6344Dichloromethane溶媒

実験手順

Rhodium (II) octanoate dimmer (0.1 equiv.) was added to a CH2Cl2 solution (0.02 M) of propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate from Step 4. The reaction mixture was stirred overnight at rt and then concentrated. The residue was purified by column chromatography on silica gel using automatized gradiant pump system CombiFlashRF (Teledyne ISCO) eluting with EtOAc/Hexane (2:98 to 10:90) to give the title compound (64%) as a yellow solid.

後処理

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on silica gel using automatized gradiant pump system CombiFlashRF (Teledyne ISCO)
  3. washeluting with EtOAc/Hexane (2:98 to 10:90)

出典と根拠

ORDレコード
ord-a20c9f11ee5d46ecafec9752809a5003
出典データセット
uspto-grants-2014_01
特許番号
US08637671B2

関連ノート

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