Ethyl Acetate → HCID 19384512, compound

HRID 2399800Notes

Reaction equation

HRID 2399800 reaction equation
C1(CO[C:9]2[CH:10]=[CH:11][CH:12]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:13]3[C:17]=2[N:16]=[C:15]2[CH2:18]CC[CH2:21][C:14]=32)C=CC=CC=1.C([O:33][CH2:34][CH3:35])(=O)C>C(O)C.[Pd]>[CH2:22]([CH:12]1[C:13]2=[C:14]3[CH2:21][CH2:35][CH:34]([OH:33])[CH2:18][C:15]3=[N:16][C:17]2=[CH:9][CH:10]=[CH:11]1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 19384567HCID 19384567, compound

Product 1

HCID 19384512HCID 19384512, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The hydrogenation of 1,2,3,4-tetrahydro-6-phenylmethoxy-9-octyl-9H-dibenzo[b,d]pyrrole from Example 63 was carried out at atmospheric pressure and at room temperature. Thus, 12.5 g of this material dissolved in 125 mL of absolute ethanol and 75 mL of ethyl acetate was hydrogenated in the presence of 0.6 g of 10% Palladium on carbon. The mixture was filtered on celite, the solvents evaporated in vacuo and the residue was chromatographed on silica gel to give 9.5 g (98.5%) of 1,2,3,4-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-3-ol as a yellow oil.

Workup

  1. customwas carried out at atmospheric pressure and at room temperature
  2. filtrationThe mixture was filtered on celite
  3. customthe solvents evaporated in vacuo
  4. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-39559bf038ad4c63bd53e75178118627
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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