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

HRID 643159Notes

Reaction equation

HRID 643159 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C@@H:21]([C:39]([OH:41])=[O:40])[CH2:22][C:23]3[CH:28]=[C:27]([CH3:29])[C:26]([O:30]CC4C=CC=CC=4)=[C:25]([CH3:38])[CH:24]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[H][H]>C(O)(C)C.[Pd]>[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C@@H:21]([C:39]([OH:41])=[O:40])[CH2:22][C:23]3[CH:28]=[C:27]([CH3:29])[C:26]([OH:30])=[C:25]([CH3:38])[CH:24]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

5

Reactant 2

HCID 68675026(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68674501(R)-2-(4-hydroxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A suspension of 600 mg (1.08 mmol) (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidine-1-carboxylate and 250 mg of 10% Pd/C in 50 mL isopropanol was hydrogenated at 50° C. and 3447 hPa hydrogen pressure for 2 h. The catalyst was suction filtered, the filtrate was evaporated down i.vac., the residue was triturated with 50 mL diethyl ether, suction filtered, washed with 20 mL diethyl ether and dried at 50° C.

Workup

  1. customwas hydrogenated at 50° C.
  2. filtrationfiltered
  3. customthe filtrate was evaporated down i.vac
  4. custom, the residue was triturated with 50 mL diethyl ether, suction
  5. filtrationfiltered
  6. washwashed with 20 mL diethyl ether
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-169763242b2e48e3889ca06012a4dcba
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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