HCID 67237589, compound → HCID 11997226, compound

HRID 1985711Notes

Reaction equation

HRID 1985711 reaction equation
C(OC([N:8]1[CH2:20][C@@H:19]2[N:11]([C:12]3[N:13]=[C:14]4[CH2:23][O:22][CH2:21][C:15]4=[CH:16][C:17]=3[CH2:18]2)[C@H:10]([CH3:24])[CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O.[O-2].[O-2].[Mn+4]>[CH3:24][C@@H:10]1[CH2:9][NH:8][CH2:20][C:19]2[N:11]1[C:12]1[N:13]=[C:14]3[CH2:23][O:22][CH2:21][C:15]3=[CH:16][C:17]=1[CH:18]=2

Participants

5

Reactant 1

HCID 67237589HCID 67237589, compound

Product 1

HCID 11997226HCID 11997226, compoundYield 31.8%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 0.050 g (5R,8aR)-5-methyl-3,5,6,8,8a,9-hexahydro-1H-2-oxa-4,4b,7-triaza-cyclopenta[b]fluorene-7-carboxylic acid tert-butyl ester in 3 ml dichloromethane was added in 4 portions in intervals of 30 min 0.20 g manganese dioxide. The mixture was then stirred at room temperature for 18 h. The product was purified by chromatography on silica gel with heptane:ethyl acetate=1:1. to yield a yellow oil which was taken up in 1 ml trifluoroacetic acid and kept at room temperature for 30 min. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The phases were separated and the aqueous phase was neutralized to pH 12 by addition of 2N sodium hydroxide and extracted with dichloromethane. The dichloromethane phase was washed with half concentrated brine and purified by chromatography on silca gel with dichloromethane:methanol:ammonia=90:10:0.1. to yield 0.011 g of the title compound as slightly yellow oil. (MS 232.1 (M+H+))

Workup

  1. customThe product was purified by chromatography on silica gel with heptane
  2. customto yield a yellow oil which
  3. waitkept at room temperature for 30 min
  4. customThe solvent was evaporated
  5. customthe residue partitioned between water and ethyl acetate
  6. customThe phases were separated
  7. additionthe aqueous phase was neutralized to pH 12 by addition of 2N sodium hydroxide
  8. extractionextracted with dichloromethane
  9. washThe dichloromethane phase was washed with half concentrated brine
  10. custompurified by chromatography on silca gel with dichloromethane

Sources & evidence

ORD record
ord-b20d928494134a6a9ceeac3913d738b4
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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