4-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-(3-Benzyl-2-cyano-5-methyl-benzofuran-7-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 18190Notes

Reaction equation

HRID 18190 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[O:21][C:20]([C:23]#[N:24])=[C:19]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:18]=3[CH:17]=[C:16]([CH3:32])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:22]3[O:21][C:20]([C:23]#[N:24])=[C:19]([CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:18]=3[CH:17]=[C:16]([CH3:32])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 593448934-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 593448834-(3-Benzyl-2-cyano-5-methyl-benzofuran-7-yl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The crude 4-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester from step 1 was dissolved in ethanol, and 10% palladium on carbon was added. The mixture was shaken under hydrogen (2.76 Bar) for 40 hours. After filtering off the catalyst, the mixture was concentrated under reduced pressure and purified using preparative thin layer chromatography (1/9 ethyl acetate/hexanes) to give 4-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe mixture was concentrated under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-21c3e9dda99549d29d9d07c694f87c79
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Reaction notes

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