HCID 14858801, compound → HCID 14858800, compound

HRID 2081953Notes

Reaction equation

HRID 2081953 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[OH:10])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[C:5]1([CH2:8][N:1]([CH2:9][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])[OH:10])=[CH:6][CH:7]=2)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 14858801HCID 14858801, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14858800HCID 14858800, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound XII (900 mg, 2.2 mmol) in 50 ml of ethyl acetate was added 10 percent palladium on activated carbon (100 mg). The reaction vessel was pressurized to 50 psi with hydrogen on a PARR hydrogenation apparatus. The reaction was complete after four hours, and was then filtered through celite and concentrated in vacuo yielding 476 mg of Compound XIII, 95 percent of the theoretical amount. This material was used without further purification in the next example. TLC Rf =0.05, 4:1 methylene chloride:hexanes.

Workup

  1. filtrationwas then filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4157d12adb3448eabe1d0d42a9acc82b
Source dataset
uspto-grants-1993_02
Patent number
US05187086

Reaction notes

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