HCID 178468194, compound → HCID 178468193, compound

HRID 1751698Notes

Reaction equation

HRID 1751698 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[CH2:8][O:9][C:10]3[CH:33]=[C:32]4[C:13]([CH2:14][CH2:15][C:16]5[N:20]=[C:19]([C@@H:21]6[CH2:25][C@H:24]([O:26][CH2:27][CH3:28])[CH2:23][N:22]6[C:29]([O-:31])=[O:30])[NH:18][C:17]=54)=[CH:12][C:11]=3[C:5]2=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[C:6]2[CH2:8][O:9][C:10]3[CH:33]=[C:32]4[C:13]([CH:14]=[CH:15][C:16]5[N:20]=[C:19]([C@@H:21]6[CH2:25][C@H:24]([O:26][CH2:27][CH3:28])[CH2:23][N:22]6[C:29]([O:31][C:5]([CH3:11])([CH3:6])[CH3:4])=[O:30])[NH:18][C:17]=54)=[CH:12][C:11]=3[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178468194HCID 178468194, compound

Product 1

HCID 178468193HCID 178468193, compoundYield 143.7%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-2-(9-chloro-1,4,5,11-tetrahydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-4-ethoxypyrrolidine-1-carboxylate (0.99 g, 1.9 mmol) in CH2Cl2 (18 mL) was added MnO2 (4.52 g, 52.0 mmol). The resulting slurry was stirred at room temperature for 18 h. The reaction was filtered through celite, washed with CH2Cl2, and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (10% to 75% EtOAc (w/5% MeOH)/Hexanes) to afford tert-butyl (2S,4S)-2-(9-chloro-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-4-ethoxypyrrolidine-1-carboxylate (0.71 g, 72%).

Workup

  1. filtrationThe reaction was filtered through celite
  2. washwashed with CH2Cl2
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by silica column chromatography (10% to 75% EtOAc (w/5% MeOH)/Hexanes)

Sources & evidence

ORD record
ord-54008c8232ba4482bfaef5306829c277
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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