4-[3-(Benzyloxy)-4-methoxyphenyl]pyrrolidin-2-one → HCID 10130484, compound

HRID 731758Notes

Reaction equation

HRID 731758 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:17]2[CH2:21][NH:20][C:19](=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1.[H][H]>CO.C(Cl)Cl.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:17]2[CH2:21][NH:20][C:19](=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

6

Reactant 2

HCID 145371514-[3-(Benzyloxy)-4-methoxyphenyl]pyrrolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 10130484HCID 10130484, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(3-Benzyloxy-4-methoxyphenyl)-2-pyrrolidone (3.5 g, 11.6 mmol) and 350 mg of 10% Pd/C in 50 mL of MeOH and 10 mL of CH2Cl2 was shaken on a Paar apparatus under a 20 psi atmosphere of hydrogen for 8 hours. The mixture was filtered through celite and concentrated to afford 2.4 g (99%) of 4-(3-Hydroxy-4-methoxyphenyl)-2-pyrrolidone that was used without further purification for the syntheses described in Examples 1-3. 1H NMR (300 MHz, CDCl3) δ 6.82 (s, 1H), 6.79 (d, J=7.6 Hz, 1H), 6.70 (d, J=7.6 Hz, 1H), 6.50 (s, 1H), 3.87 (s, 3H), 3.77 (t, J=8.4 Hz, 1H), 3.62 (t, J=8.0 Hz, 1H), 3.40 (t, J=8.4 Hz, 1H), 2.71 (dd, J=16.8, 8.8 Hz, 1H), 2.49 (dd, J=16.8, 9.0 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-cbf67bf62bc24329935004fee652b54c
Source dataset
uspto-grants-2009_09
Patent number
US07585882B2

Reaction notes

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