Triethylamine → HCID 18689930, compound

HRID 1871924Notes

Reaction equation

HRID 1871924 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O.C(N(CC)CC)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18689928HCID 18689928, compound

Product 1

HCID 18689930HCID 18689930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-tert-Butoxycarbonyl-4-hydroxy-4-(2-quinolylmethyl)piperidine (5.95 g) was dissolved in anhydrous THF (50 ml), and methane sulfonylchloride (2.99 g) and triethylamine (7.3 ml) were added to the solution. The mixture was stirred at room temperature for two hours and concentrated under reduced pressure. Water and ethyl acetate were added to the mixture to thereby separate an organic phase, which was further washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure. The residue was dissolved in toluene (50 ml), and DBU (5.30 g) was added to the solution. The mixture was stirred at 60° C. for three hours and concentrated under reduced pressure. Water and ethyl acetate were added to the mixture to thereby separate an organic phase, which was further washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (developer: hexane-ethyl acetate (1:1)). The title compound was obtained through crystallization from hexane.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater and ethyl acetate were added to the mixture
  3. customto thereby separate an organic phase, which
  4. washwas further washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in toluene (50 ml)
  8. additionDBU (5.30 g) was added to the solution
  9. stirringThe mixture was stirred at 60° C. for three hours
  10. concentrationconcentrated under reduced pressure
  11. additionWater and ethyl acetate were added to the mixture
  12. customto thereby separate an organic phase, which
  13. washwas further washed with saturated brine
  14. dry with materialdried over sodium sulfate anhydrate
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e6b31046421432fa26f3e8cc7d6e6a5
Source dataset
uspto-grants-2000_08
Patent number
US06107308

Reaction notes

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