Trifluoroacetic acid → HCID 86721004, compound

HRID 524948Notes

Reaction equation

HRID 524948 reaction equation
C(O)(C(F)(F)F)=O.[N+:8]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[C:17]1[CH2:18][CH2:19][N:20](C(OC(C)(C)C)=O)[CH2:21][CH:22]=1)([O-:10])=[O:9]>C(Cl)Cl>[N+:8]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[C:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86721003HCID 86721003, compound

Product 1

HCID 86721004HCID 86721004, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL, 25.96 mmol) was added to a stirred solution of tert-butyl 4-(3-nitro-4-pyridyl)-3,6-dihydro-2H-pyridine-1-carboxylate (883 mg, 2.892 mmol) in DCM (10 mL) and the reaction stirred at ambient temperature for 15 hours. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and ether (×2). The residue was passed through a 25 g SCX-2 cartridge and washed with MeOH/DCM mixtures. The product was eluted by washing the cartridge with 2M NH3 in MeOH/DCM mixtures and concentrated in vacuo to give 3′-nitro-1,2,3,6-tetrahydro-4,4′-bipyridine as an orange oil (523 mg, 88% Yield). MS (ES+) 206.1.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with DCM (×2) and ether (×2)
  3. washwashed with MeOH/DCM
  4. washThe product was eluted
  5. washby washing the cartridge with 2M NH3 in MeOH/DCM mixtures
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df29634d9c454181a9a5b1785e9c3929
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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