Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate → Methyl 2-(1-pyrrolidinylmethyl)-4-piperidinecarboxylate

HRID 1196512Notes

Reaction equation

HRID 1196512 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Rh]>[N:1]1([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][NH:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 15123252Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

Product 1

HCID 19898871Methyl 2-(1-pyrrolidinylmethyl)-4-piperidinecarboxylateYield 35%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of stage (iv) (50 mg) in ethanol (2 ml) was hydrogenated at 70 psi and 70° over 5% rhodium on carbon (35 mg) for 14 h. The mixture was filtered and the filtrate was evaporated in vacuo. The residue (0.1 g) was purified by flash chromatography eluting with dichloromethane/methanol/ammonia 200:10:2 to give the title compound as an oil (0.018 g). T.l.c. (Silica/dichloromethane/methanol/ammonia 75:10:2) Rf 0.6.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue (0.1 g) was purified by flash chromatography
  4. washeluting with dichloromethane/methanol/ammonia 200:10:2

Sources & evidence

ORD record
ord-2b673f4d9e2b4668b73eb4cd646ecaa5
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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