HCID 86620145, compound → HCID 86620144, compound

HRID 1664924Notes

Reaction equation

HRID 1664924 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:15][N:14]2[C:16]([CH3:19])=[N:17][CH2:18][CH:13]2[C@H:12]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:11][CH2:10]1>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:15][N:14]2[C:16]([CH3:19])=[N:17][CH:18]=[C:13]2[C@H:12]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 86620145HCID 86620145, compound

Product 1

HCID 86620144HCID 86620144, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

Manganese(IV) oxide (46.0 mg, 0.53 mmol) was added to a solution of tert-butyl [(6S,9R)-6-(2,3-difluorophenyl)-3-methyl-5,6,7,8,9,9a-hexahydro-1H-imidazo[1,5-a]azepin-9-yl]carbamate (20.0 mg, 0.053 mmol) in toluene (7 mL). The reaction mixture was heated to reflux. After 8 h, additional manganese (IV) oxide (46.0 mg, 0.53 mmol) was added. After 16 h, the reaction mixture was allowed to cool to ambient temperature. The mixture was filtered, washed with methanol, and concentrated. Purification by preparative thin layer chromatography (9% methanol/dichloromethane) gave the title compound (5 mg). MS 378.1 (M+1).

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. waitAfter 16 h
  3. filtrationThe mixture was filtered
  4. washwashed with methanol
  5. concentrationconcentrated
  6. customPurification by preparative thin layer chromatography (9% methanol/dichloromethane)

Sources & evidence

ORD record
ord-22b51e5ca1ee408fb693a61e58bef9f8
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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