3',6'-dihydro-2'H-[3,4']bipyridinyl-4,1'-dicarboxylic acid 1'-t-butyl ester 4-methyl ester → HCID 58442838, compound

HRID 41624Notes

Reaction equation

HRID 41624 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=1)=[O:4]>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]1)=[O:4]

Participants

4

Reactant 1

HCID 584428153',6'-dihydro-2'H-[3,4']bipyridinyl-4,1'-dicarboxylic acid 1'-t-butyl ester 4-methyl ester

Product 1

HCID 58442838HCID 58442838, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd(OH)2/C (0.4 g) was added to a solution of 3′,6′-dihydro-2′H-[3,4′]bipyridinyl-4,1′-dicarboxylic acid 1′-t-butyl ester 4-methyl ester (500 mg, 1.2 mmol, 1.0 eq.) in EtOAc (15 mL), maintained under hydrogen at 1 atm. The resulting solution was stirred over night at room temperature. The solids were filtered. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:3) to yield 3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-4,1′-dicarboxylic acid 1′-t-butyl ester 4-methyl ester (240 mg) as a colorless liquid.

Workup

  1. temperaturemaintained under hydrogen at 1 atm
  2. filtrationThe solids were filtered
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. washeluted with EtOAc/PE (1:3)

Sources & evidence

ORD record
ord-5b340e2794cc40b8842ac0fff88f1ff1
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

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