HCID 178451674, compound → HCID 178451671, compound

HRID 1751599Notes

Reaction equation

HRID 1751599 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[CH2:8][O:9][C:10]3[CH:34]=[C:33]4[C:13]([CH2:14][CH2:15][C:16]5[N:20]=[C:19]([CH:21]6[CH2:25][CH2:24][CH2:23][N:22]6[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[NH:18][C:17]=54)=[CH:12][C:11]=3[C:5]2=[CH:4][CH:3]=1>ClCCl.C(OCC)(=O)C.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:7]=[C:6]2[CH2:8][O:9][C:10]3[CH:34]=[C:33]4[C:13]([CH:14]=[CH:15][C:16]5[N:20]=[C:19]([CH:21]6[CH2:25][CH2:24][CH2:23][N:22]6[C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[NH:18][C:17]=54)=[CH:12][C:11]=3[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 178451674HCID 178451674, compound

Product 1

HCID 178451671HCID 178451671, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(9-chloro-1,4,5,11-tetrahydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.9 g, 3.96 mmol) in dichloromethane (35 mL) was added manganese(IV) oxide (17 g, 198 mmol). The reaction mixture was stirred at room temperature for 18 hours, diluted with ethyl acetate. The organics were washed with water and brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography to yield tert-butyl 2-(9-chloro-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.52 g, 81%). LCMS-ESI+: calculated for C27H26ClN3O342: 475.9; observed [M+1]+: 476.45.

Workup

  1. washThe organics were washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-cff553f1f0cd4ab1b5be2d2254ddf048
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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