3,6-dihydro-2H-[4,4]bipyridinyl-1,3'-dicarboxylic acid 1-t-butyl ester 3'-methyl ester → Methyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)nicotinate

HRID 41620

Reaction equation

HRID 41620 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=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].[H][H]>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=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

5

Reactant 2

HCID 584428293,6-dihydro-2H-[4,4]bipyridinyl-1,3'-dicarboxylic acid 1-t-butyl ester 3'-methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 58442809Methyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)nicotinateYield 76.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Pd(OH)2/C (5.2 g, 7.4 mmol, 0.3 eq., 20%) in EtOAc (100 mL) was stirred for 10 minutes at room temperature under nitrogen. 3,6-Dihydro-2H-[4,4′]bipyridinyl-1,3′-dicarboxylic acid 1-t-butyl ester 3′-methyl ester (8.7 g, 27.3 mmol, 1.0 eq.) was added. Hydrogen gas was introduced into the reaction vessel (at 1 atm) and the solution was stirred for 5 hours at room temperature. The solids were filtered and the resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:5) to yield 3,4,5,6-tetrahydro-2H-[4,4′]bipyridinyl-1,3′-dicarboxylic acid 1-t-butyl ester 3′-methyl ester (6.7 g) as a colorless oil.

Workup

  1. filtrationThe solids were filtered
  2. concentrationthe resulting mixture was concentrated under vacuum
  3. washeluted with EtOAc/PE (1:5)

Sources & evidence

ORD record
ord-c9b3700b34684366a734314c04cac608
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Linked notes

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