(Diethylamino)sulfur trifluoride → HCID 54319796, compound

HRID 617350Notes

Reaction equation

HRID 617350 reaction equation
[CH3:1][N:2]1[CH2:6][C@H:5](O)[CH2:4][C@H:3]1[CH2:8][O:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.CCN(S(F)(F)[F:22])CC>C(Cl)Cl>[F:22][C@@H:5]1[CH2:6][N:2]([CH3:1])[C@H:3]([CH2:8][O:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 18391713HCID 18391713, compound

Product 1

HCID 54319796HCID 54319796, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 100 mg (0.5 mmol) sample of 3-((trans-1-methyl-4-hydroxy-2(S)-pyrrolidinyl)methoxy)pyridine, from Example 23 above, above was dissolved in 10 mL of methylene chloride and cooled to -78° C. To this was added 0.165 mL (1.25 mmol) of DAST, and the mixture was stirred for 4 hours while allowing the reaction mixture to warm to room temperature. The reaction was quenched by addition of satd NaHCO3 solution, and the mixture was extracted with chloroform. The solvent was removed, and the residue was purified by chromatography on silica gel, eluting with 20:1 CHCl3 :methanol, to give 30 mg of title compound.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched by addition of satd NaHCO3 solution
  3. extractionthe mixture was extracted with chloroform
  4. customThe solvent was removed
  5. customthe residue was purified by chromatography on silica gel
  6. washeluting with 20:1 CHCl3

Sources & evidence

ORD record
ord-31e3370f8c33486c8f327dbf5a74183f
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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