(Diethylamino)sulfur trifluoride → Ammonia

HRID 1416649Notes

Reaction equation

HRID 1416649 reaction equation
O[CH2:2][CH:3]1[CH2:7][N:6]([CH3:8])[C@H:5]([CH2:9][O:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:4]1.CCN(S(F)(F)[F:23])CC>C(Cl)Cl>[NH3:6].[F:23][CH2:2][C@@H:3]1[CH2:7][N:6]([CH3:8])[C@H:5]([CH2:9][O:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:4]1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 53783690HCID 53783690, compound

Product 2

HCID 222AmmoniaHCID 21309642HCID 21309642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 1.57 g (7.1 mmol) sample of 3-((4-hydroxymethyl-1-methyl-2-(S)-pyrrolidinyl)methoxy)pyridine, prepared as described in Example 48b above, was dissolved in 40 mL of methylene chloride, and the solution was cooled to -78° C. To this solution was added 2.80 mL (21.2 mmol) of DAST, then the solution was stirred at -35° C. for 1.5 hours. The reaction mixture was warmed to room temperature, and the reaction was quenched by the addition of satd NaHCO3. The mixture was extracted with chloroform, the solvent was removed, and the residue was purified on a silica gel column, eluting with 100:2 chloroform:methanol to 10:1:0.02 chloroform:methanol:ammonia, to give 120 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customthe reaction was quenched by the addition of satd NaHCO3
  3. extractionThe mixture was extracted with chloroform
  4. customthe solvent was removed
  5. customthe residue was purified on a silica gel column
  6. washeluting with 100:2 chloroform

Sources & evidence

ORD record
ord-6f32aa0a39e9444ea16cbe0a1ee697a6
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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