Triethylamine → HCID 21083282, compound

HRID 347630Notes

Reaction equation

HRID 347630 reaction equation
[N:1]([CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1)=[N+]=[N-].C(N(CC)CC)C.[O:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=O>CO.[Pd]>[C:26]([O:25][C:23]([NH:1][CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1)=[O:22])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 22565575Methyl 6-(azidomethyl)nicotinate

Product 1

HCID 21083282HCID 21083282, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a degassed solution of methyl 6-(azidomethyl)nicotinate from Example G2 (1.6 g, 8.30 mmol) in methanol (50 ml) was added 10% palladium-on-carbon (0.15 g). Hydrogen gas was bubbled through the mixture for 2 h at room temperature. The catalyst was removed by filtration through a pad of celite and the filtrate was evaporated in vacuo. The residue was dissolved in dichloromethane and cooled to 0° C. To this solution were added triethylamine (1.67 g, 16.0 mmol) and (BOC)2O (2.17 g, 9.96 mmol). The mixture was allowed to warm to room temperature and stirred for 18 h, then concentrated in vacuo. The residue was dissolved in EtOAc and washed with water, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 50:50) to give a yellow solid; yield 1.57 g (71%).

Workup

  1. customHydrogen gas was bubbled through the mixture for 2 h at room temperature
  2. customThe catalyst was removed by filtration through a pad of celite
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. temperatureto warm to room temperature
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in EtOAc
  8. washwashed with water
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 50:50)
  12. customto give a yellow solid

Sources & evidence

ORD record
ord-5187f843e33a439e9d6ffae8ca80d40b
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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