(Diethylamino)sulfur trifluoride → Ammonia

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence