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 475487

Reaction equation

HRID 475487 reaction equation
[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-]>CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh].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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6099591Rhodium(II) Octanoate DimerCatalystHCID 6344DichloromethaneSolvent

Procedure

Rhodium (II) octanoate dimer (0.1 equiv.) was added to a CH2Cl2 solution (0.02 M) of propyl [2-(4-diazo-3-oxobutyl)-1H-indo1-3-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 a CombiFlashRF (Teledyne ISCO) eluting with EtOAc/Hex (2:98 to 10:90) to give the title compound (64%) as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-b2282c4428c64bca84ee603e25739878
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Linked notes

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