Cornforth reagent → HCID 59722739, compound

HRID 1664853Notes

Reaction equation

HRID 1664853 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=1[C@H:30]1[CH2:36][N:35]2[C:37]([CH:40]([OH:42])[CH3:41])=[CH:38][N:39]=[C:34]2[C@H:33]([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH2:32][CH2:31]1>C(#N)C>[C:40]([C:37]1[N:35]2[CH2:36][C@H:30]([C:24]3[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:23]=3[F:22])[CH2:31][CH2:32][C@@H:33]([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:34]2=[N:39][CH:38]=1)(=[O:42])[CH3:41]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 59722677HCID 59722677, compound

Product 1

HCID 59722739HCID 59722739, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridinium dichromate (0.96 g, 2.55 mmol) was added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-(1-hydroxyethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (0.52 g, 1.28 mmol) in acetonitrile (10 mL). After 18 h, the reaction was filtered through celite and concentrated. Saturated sodium carbonate was added and the mixture was extracted with dichloromethane (3×). The organic layer was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→40% ethyl acetate/dichloromethane) gave the title compound (0.38 g). MS 406.1 (M+1).

Workup

  1. filtrationthe reaction was filtered through celite and
  2. concentrationconcentrated
  3. additionSaturated sodium carbonate was added
  4. extractionthe mixture was extracted with dichloromethane (3×)
  5. washThe organic layer was washed with water, saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (100% dichloromethane→40% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-b2073dc2d5cd46eeab95f1325ea96e0e
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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