(R)-1-carboxy-2-(4-benzyloxy-3,5-dimethyl-phenyl)-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate → (R)-1-carboxy-2-(4-hydroxy-3,5-dimethyl-phenyl)-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate

HRID 643155Notes

Reaction equation

HRID 643155 reaction equation
[O:1]=[C:2]1[N:14]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C@@H:24]([C:42]([OH:44])=[O:43])[CH2:25][C:26]3[CH:31]=[C:30]([CH3:32])[C:29]([O:33]CC4C=CC=CC=4)=[C:28]([CH3:41])[CH:27]=3)=[O:22])[CH2:17][CH2:16]2)[C:5]2[CH:6]=[N:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:4]=2[NH:3]1.[H][H]>C1COCC1.CO.[Pd]>[O:1]=[C:2]1[N:14]([CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C@@H:24]([C:42]([OH:44])=[O:43])[CH2:25][C:26]3[CH:27]=[C:28]([CH3:41])[C:29]([OH:33])=[C:30]([CH3:32])[CH:31]=3)=[O:22])[CH2:19][CH2:20]2)[C:5]2[CH:6]=[N:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:4]=2[NH:3]1

Participants

6

Reactant 2

HCID 68675784(R)-1-carboxy-2-(4-benzyloxy-3,5-dimethyl-phenyl)-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68673716(R)-1-carboxy-2-(4-hydroxy-3,5-dimethyl-phenyl)-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1.80 g (3.03 mmol) (R)-1-carboxy-2-(4-benzyloxy-3,5-dimethyl-phenyl)-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate and 300 mg 10% Pd/C in 30 mL THF and 30 mL MeOH was hydrogenated at 3000 hPa hydrogen pressure and RT for 48 h. The catalyst was suction filtered, the filtrate was evaporated down and the residue was purified by HPLC; the fractions containing the product were combined and lyophilised.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated down
  3. customthe residue was purified by HPLC
  4. additionthe fractions containing the product

Sources & evidence

ORD record
ord-134ff46920fb48e6b7a97f9a3ffc282c
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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