HCID 15884726, compound → HCID 15884727, compound

HRID 379516Notes

Reaction equation

HRID 379516 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[N:5]1C(OCC1C=CC=CC=1)=O>CO.[Pd]>[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[NH:5]1

Participants

4

Reactant 1

HCID 15884726HCID 15884726, compound

Product 1

HCID 15884727HCID 15884727, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methoxymethyl-5-(2-methoxyphenyl)-N-(carbobenzyloxy)-tetrahydropyrrole (1.3 g, 3.66 mmol) in methanol (40 mL) was added 10% Pd-C (1.3 g) and the resulting suspension was hydrogenated (50 psi) for 3 hours. Pd-C was then filtered off and the crude reaction mixture was concentrated in vacuo to give a yellowish residue, which was purified by silica gel flash chromatography (5% MeOH-0.5% NH3♦H2O-94.5% CH2Cl2) to afford the title compound as a colorless oil (439.2 mg, 54%). MS m/z: 222 (M+H).

Workup

  1. customfor 3 hours
  2. filtrationPd-C was then filtered off
  3. customthe crude reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customto give a yellowish residue, which
  6. customwas purified by silica gel flash chromatography (5% MeOH-0.5% NH3♦H2O-94.5% CH2Cl2)

Sources & evidence

ORD record
ord-9c00ace4466845f7a24e9e7418277d13
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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