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

반응식

HRID 476226 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 10178397Rhodium(II) octanoate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a20c9f11ee5d46ecafec9752809a5003
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637671B2

연결된 노트

불러오는 중…