3-(Benzyloxy)-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one → 3-Hydroxy-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one

HRID 625946Notes

Reaction equation

HRID 625946 reaction equation
C([O:8][C:9]1[C:10](=[O:28])[N:11]([CH3:27])[CH:12]=[C:13]([N:15]2[CH2:19][CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17][C:16]2=[O:26])[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:10](=[O:28])[N:11]([CH3:27])[CH:12]=[C:13]([N:15]2[CH2:19][CH:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:17][C:16]2=[O:26])[CH:14]=1

Participants

4

Reactant 1

HCID 674205813-(Benzyloxy)-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one

Product 1

HCID 533798133-Hydroxy-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-oneYield 59.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(Benzyloxy)-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one (131 mg, 0.350 mmol) was hydrogenated (balloon) with 10% Pd/C (37 mg, 0.035 mmol) in MeOH (3 mL) at RT. After stirring overnight the mixture was filtered using a 0.45 μm PTFE syringe filter then purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-50% CH3CN/water over 20 min at 20 mL/min) to give the title compound (59 mg, 59%) as an off-white solid. 1H NMR (500 MHz, CDCl3): δ 7.52 (d, J=2.6 Hz, 1 H); 7.40-7.28 (m, 5 H); 6.98 (d, J=2.6 Hz, 1 H); 4.08 (t, J=8.4 Hz, 1 H); 3.77-3.66 (m, 2 H); 3.64 (s, 3 H); 2.99 (m, 1 H); 2.76 (m, 1 H). HRMS (ES) calc (M+H)+=285.1234, found 285.1228.

Workup

  1. customat RT
  2. filtrationwas filtered
  3. filtrationfilter
  4. customthen purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-50% CH3CN/water over 20 min at 20 mL/min)

Sources & evidence

ORD record
ord-bf41c132bfc64cb1b64e8538e356c008
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

Loading…