HCID 69193806, compound → HCID 59772441, compound

HRID 2220211Notes

Reaction equation

HRID 2220211 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][N:11](C(=O)C)[C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[CH:8]([OH:20])[CH2:7][C:6]=2[CH:21]=1>CO.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][NH:11][C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[C:8](=[O:20])[CH2:7][C:6]=2[CH:21]=1

Participants

4

Reactant 1

HCID 69193806HCID 69193806, compound

Product 1

HCID 59772441HCID 59772441, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of 1-(9-Bromo-1 2-hydroxy-11,12-dihydro-6H-dibenzo[b,f]azocin-5-yl)-ethanone (prepared similar to Example 1E using the appropriate starting materials) (50 mg, 0.17 mmol) in MeOH (5 mL) was added MnO2 (72 mg, 0.83 mmol). The mixture was stirred under argon for 36 hours, filtered, and the filtrate was concentrated. The resulting residue was dissolved in THF (5 mL), MnO2 (144 mg, 1.66 mmol) was added, and the resulting mixture was stirred at room temperature overnight. The suspension was filtered, concentrated and purified by flash chromatography (SiO2, 15% EtOAc/hexanes) to afford Example 213A (25 mg, 49%) as an off-white solid.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe resulting residue was dissolved in THF (5 mL)
  4. stirringthe resulting mixture was stirred at room temperature overnight
  5. filtrationThe suspension was filtered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (SiO2, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2c9c9133bd3043b0a9912c3c621262e6
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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