(Diethylamino)sulfur trifluoride → HCID 68953227, compound

Participants

Reaction Steps

Cool a solution of (4-bromo-phenyl)-(1-methyl-pyrrolidin-3-yl)-methanol in CH2Cl2 (6.5 mL) to 0° C. Add slowly a solution of DAST (0.1 mL, 0.78 mmol) in CH2Cl2. Stir the mixture at RT overnight. Cool the mixture to 0° C., then carefully quench with saturated NaHCO3 (exothermic and gas evolution). Extract the aqueous layer with CH2Cl2. Dry the combined organic phases with Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, collecting all the fractions as the product does not show by UV. Elute with 5-10% MeOH (2 N NH3)/CH2Cl2 to give 0.049 g (35%) of the title compound. LC-MS/ES m/z (79Br) 272.0 [M+H]+.

Provenance & Evidence