HCID 86758055, compound → HCID 57168096, compound

HRID 1934564Notes

Reaction equation

HRID 1934564 reaction equation
C1(N(C2C=CC=CC=2)C(OCC23OC2(OCC(OCC)=O)C2C=CC=CC=2CCC3)=O)C=CC=CC=1.[C:37]1([N:43]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[C:44]([O:46][CH2:47][C:48]23[O:55][CH:54]2[CH2:53][CH2:52][C:51]2[C:56]([O:60][CH2:61][C:62]([O:64][CH2:65][CH3:66])=[O:63])=[CH:57][CH:58]=[CH:59][C:50]=2[CH2:49]3)=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CCOC(C)=O.[Pd]>[C:37]1([N:43]([C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[C:44]([O:46][CH2:47][C:48]2([OH:55])[CH2:54][CH2:53][CH2:52][C:51]3[C:56]([O:60][CH2:61][C:62]([O:64][CH2:65][CH3:66])=[O:63])=[CH:57][CH:58]=[CH:59][C:50]=3[CH2:49]2)=[O:45])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1.[C:67]1([N:43]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:44]([O:46][CH2:47][C:48]23[O:55][CH:54]2[CH2:53][CH2:52][C:51]2[C:56]([O:60][CH2:61][C:62]([O:64][CH2:65][CH3:66])=[O:63])=[CH:57][CH:58]=[CH:59][C:50]=2[CH2:49]3)=[O:45])[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=1

Participants

6

Reactant 2

HCID 86758055HCID 86758055, compoundHCID 86758056HCID 86758056, compound

Product 2

HCID 57168096HCID 57168096, compoundHCID 86758055HCID 86758055, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of a mixture of ethyl {[6-(N,N-diphenyl-carbamoyloxy)methyl-5,6-epoxy-6,7,8,9-tetrahydro-5H-benzo-cyclohepten-5-yl]oxy}acetate and ethyl {[6-(N,N-diphenyl-carbamoyloxy) methyl-6,7-epoxy-6,7,8,9-tetrahydro-5H-benzo-cyclohepten-1-yl]oxy}acetate (265 mg) in EtOAc (13 ml) was added 10% Pd—C (wet) (80 mg). The mixture was stirred under hydrogen atmosphere at room temperature for 6 hours. After removal of the catalyst by filtration, the filtrate was evaporated. The residue was purified by silica gel column chromatography (hexane-EtOAc 2:1 to 1:1) to give ethyl {[6-(N,N-diphenylcarbamoyloxy)methyl-6-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yl]oxy}acetate (193.3 mg) as a solid and ethyl {[6-(N,N-diphenylcarbamoyloxy) methyl-6,7-epoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yl]oxy}acetate (60.0 mg) as an oil.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated
  4. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 2:1 to 1:1)

Sources & evidence

ORD record
ord-cb888c23f2ca49b5a2ef5c167ef7957d
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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