Triethylamine → HCID 86603235, compound

HRID 1354230Notes

Reaction equation

HRID 1354230 reaction equation
C(N(CC)CC)C.CS(Cl)(=O)=O.O[CH2:14][C:15]1[CH2:20][N:19]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17][CH:16]=1.C([O-])(O)=O.[Na+].[N-:34]=[N+:35]=[N-:36].[Na+]>C(Cl)Cl>[N:34]([CH2:14][C:15]1[CH2:20][N:19]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17][CH:16]=1)=[N+:35]=[N-:36]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 69520111HCID 69520111, compound

Product 1

HCID 86603235HCID 86603235, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

At 0° C., triethylamine (3.7 ml, 26.2 mmol) and, dropwise, methanesulphonyl chloride (1.2 ml, 15.44 mmol) were added to a solution of tert-butyl 5-hydroxymethyl-3,6-dihydro-2H-pyridine-1-carbamate (Tetrahedron 1998, 54, 7045–7056, 2.8 g, 13.1 mmol) in DCM (50 ml). The reaction mixture was stirred at 0° C. for 20 minutes before a saturated solution of NaHCO3 (40 ml) was added, and the two phases were separated. The aqueous phase was extracted with dichloromethane (40 ml). The combined organic phases were washed with saturated sodium chloride solution and dried over MgSO4 and concentrated. The crude product was dissolved in DMF (50 ml), and sodium azide (1.7 g, 26.1 mmol) was added. The mixture was heated to 80° C. Reaction monitored by LCMS. Once the reaction was complete, the mixture was cooled and concentrated. The residue was taken up in EtOAc and water and the aqueous phase was extracted with EtOAc (2×100 ml). The combined organic phases were washed with saturated sodium chloride solution, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel (EtOAc/hex 1/6).

Workup

  1. additionwas added
  2. customthe two phases were separated
  3. extractionThe aqueous phase was extracted with dichloromethane (40 ml)
  4. washThe combined organic phases were washed with saturated sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. dissolutionThe crude product was dissolved in DMF (50 ml)
  8. customReaction
  9. temperaturethe mixture was cooled
  10. concentrationconcentrated
  11. extractionwater and the aqueous phase was extracted with EtOAc (2×100 ml)
  12. washThe combined organic phases were washed with saturated sodium chloride solution
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated
  15. customThe residue was purified by chromatography on silica gel (EtOAc/hex 1/6)

Sources & evidence

ORD record
ord-1802a08561534e0e911374d1b8f5c63a
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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