Methanol → HCID 67125897, compound

HRID 929967Notes

Reaction equation

HRID 929967 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([O-:22])=[O:21])=[N:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H].[CH3:25]O>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([O:22][CH3:25])=[O:21])=[N:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 86702368HCID 86702368, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67125897HCID 67125897, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

5-(1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)picolinate from Step 1 (250 mg, 0.79 mmol) was taken up in MeOH/EtOAC (3:1, v/v) and 10% Pd/C (50 mg) was added. The resulting mixture was hydrogenation with a hydrogen balloon at rt for over night. Hydrogenation continued for another 3 h at 55° C. LC-MS indicated that the reaction was complete. The reaction mixture was filtered over a celite plug and washed with MeOH. The filtrate was evaporated under reduced pressure and dried in vacuum oven to give methyl 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)picolinate (250 mg, 100%). LC-MS (ESI) m/z 321 (M+H)+.

Workup

  1. customat rt
  2. filtrationThe reaction mixture was filtered over a celite plug
  3. washwashed with MeOH
  4. customThe filtrate was evaporated under reduced pressure
  5. customdried in vacuum oven

Sources & evidence

ORD record
ord-139ba16cfd36424d8125e27330770b50
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Reaction notes

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