Hydrochloric Acid → HCID 86758060, compound

HRID 1934568Notes

Reaction equation

HRID 1934568 reaction equation
[C:1]1([N:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]([O:10][CH2:11][CH:12]2[CH2:18][CH2:17][CH2:16][C:15]3[C:19]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:21]=[CH:22][C:14]=3[C:13]2=[O:30])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.Cl>[OH-].[OH-].[Pd+2].CCO>[C:1]1([N:7]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:8]([O:10][CH2:11][CH:12]2[CH2:18][CH2:17][CH2:16][C:15]3[C:19]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:21]=[CH:22][C:14]=3[CH:13]2[OH:30])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 9891631HCID 9891631, compound

Product 1

HCID 86758060HCID 86758060, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl {[6-(N,N -diphenylcarbamoyloxy)methyl-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yl]oxy}acetate (100 mg) in a mixed solvent of THF and EtOH (1:4, 5 ml) were added 20% Pd(OH)2 on carbon and catalytic amount of concentrated hydrochloric acid. The mixture was hydrogenated for 5 hours at 3 atm. After removal of the catalyst by filtration, the filtrate was evaporated. The residue was dissolved in EtOAc, washed with saturated sodium hydrogencarbonate solution, water, and then brine. It was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 2:1) to give ethyl {[(5SR,6RS)-6-(N,N-diphenylcarbamoyloxy) methyl-5-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yl]oxy}acetate (22.0 mg) as an amorphous solid.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with saturated sodium hydrogencarbonate solution, water
  6. dry with materialIt was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 2:1)

Sources & evidence

ORD record
ord-df862e52992d4700b52aca746db3656c
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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