(2S)-1-amino-3-methoxypropan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Suspend sodium hydride (60% in mineral oil, 13.56 g, 339.1 mmol) in dimethylacetamide (245.7 mL) and add a solution of (2S)-1-amino-3-methoxy-2-propanol (31.0 g, 147.4 mmol) in dimethylacetamide (59.0 mL) over 30 minutes. Stir for one hour; then add 2,5-difluoropyridine (17.03 mL, 162.17 mmol) over a 30 min interval; and stir at ambient temperature for an additional 1.5 hours. Slowly add water (930 mL) to quench the reaction. Extract the resulting mixture with EtoAc (4×300 mL) and combine the organic extracts. Dry the combined extracts over magnesium sulfate; filter and concentrate the filtrate under reduced pressure. Purify via flash column chromatography using a gradient of 0 to 10% EtOAc in DCM to give the title compound as a brown oil (12.0 g). MS (m/z): 201 (M+1). and stir at ambient temperature for an additional 1.5 hours Slowly add water (930 mL) to quench the reaction Extract the resulting mixture with EtoAc (4×300 mL) Dry the combined extracts over magnesium sulfate filter concentrate the filtrate under reduced pressure Purify via flash column chromatography