HCID 58442810, compound → HCID 58442811, compound

HRID 41627Notes

Reaction equation

HRID 41627 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=2)=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:4].[H][H]>[OH-].[OH-].[Pd+2].CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 2

HCID 58442810HCID 58442810, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58442811HCID 58442811, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd(OH)2/C (690 mg) was added to a solution of 3′,6′-dihydro-2′H-[2,4]bipyridinyl-3,1′-dicarboxylic acid 1′-t-butyl ester 3-methyl ester (2.0 g, 6.3 mmol, 1.0 eq.) in PE (220 mL) and EtOAc (50 mL). Hydrogen gas (1 atm) was introduced into the reaction vessel, and the solution was stirred for 20 hours at room temperature. The reaction mixture was filtered and the remaining mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:8) to yield 3′,4′,5′,6′-tetrahydro-2′H-[2,4]bipyridinyl-3,1′-dicarboxylic acid 1′-t-butyl ester 3-methyl ester (1.2 g) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe remaining mixture was concentrated under vacuum
  3. washeluted with EtOAc/PE (1:8)

Sources & evidence

ORD record
ord-67c3c583cbd4498ea95d504ee0646e9b
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

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