Methanol → 1-Tert-butyl 4-methyl 1,2,3,6-tetrahydropyridine-1,4-dicarboxylate

HRID 1247034Notes

Reaction equation

HRID 1247034 reaction equation
[C:1]([N:8]1[CH2:13][CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:29][OH:30].CN(C)[CH:33]=[O:34]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:29]([O:34][CH3:33])=[O:30])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 118067821-Tert-butyl 4-methyl 1,2,3,6-tetrahydropyridine-1,4-dicarboxylateYield 65%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

To a stirred solution of 1-Boc-1,2,3,6-tetrahydro-4-[(trifluoromethyl)sulfonyloxy]pyridine (74.84 g, 226 mmol) in N,N-dimethylformamide (60 mL) was added triethylamine (4.2 mL, 30.2 mmol), palladium acetate (0.100 g, 0.45 mmol), triphenylphosphine (0.235 g, 0.9 mmol), and methanol (24.5 mL) and the solution was placed under an atmosphere of carbon monoxide. After stirring for 48 h, the solvent was removed in vacuo. The residue was chromatographed over silica gel, eluting with 5–10% ethyl acetate in hexane. The product containing fractions were combined and concentrated in vacuo to give 2.35 g (65%) of the title compound as a clear oil.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was chromatographed over silica gel
  3. washeluting with 5–10% ethyl acetate in hexane
  4. additionThe product containing fractions
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-935dd3ee3c38450b9eaf32d5560d4476
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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