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(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 491169
Notes
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Reaction equation

HRID 491169 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23938PalladiumCatalyst
HCID 3776
Isopropanol
Solvent

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-9a727d2a107c484d863cb296594d9481
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528129B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes