tert-Butyl 4-(2-methyl-3-pyridyl)-3,6-dihydro-2H-pyridine-1-carboxylate → tert-Butyl 4-(2-methyl-3-pyridyl)piperidine-1-carboxylate

HRID 1775348Notes

Reaction equation

HRID 1775348 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1>C(O)C.[H][H]>[CH3:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 121257689tert-Butyl 4-(2-methyl-3-pyridyl)-3,6-dihydro-2H-pyridine-1-carboxylate

Product 1

HCID 131734738tert-Butyl 4-(2-methyl-3-pyridyl)piperidine-1-carboxylateYield 47.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

tert-Butyl 4-(2-methyl-3-pyridyl)-3,6-dihydro-2H-pyridine-1-carboxylate (209 mg, 0.76 mmol) was dissolved in ethanol (42 ml) and hydrogenated in a H-cube hydrogen generator with a flow of 1 ml/min and at a temperature of 70° C. The mixture was evaporated under reduced pressure, the residue was purified by preparative HPLC (Waters X-Bridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 100 mg of a colourless solid (0.36 mmol, yield 47%). MS (ESI) m/z=277.2 [M+1]+.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue was purified by preparative HPLC (Waters X-Bridge, gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-b5f02792976a40629e93998750c1237b
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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