Hydroxylamine → (R)-2-(tert-Butyl)-2-methyl-1-tosylaziridine

Participants

Reaction Steps

A solution of the amino alcohol from Step 2 (4.98 g, 38.0 mmol) in CH2Cl2 (200 mL) at 0° C. was treated with Et3N (26 mL, 190 mmol) followed by a solution of p-toluenesulfonyl chloride (8.7 g, 45.6 mmol) in CH2Cl2 (50 mL) over 40 min. The reaction mixture was stirred at room temperature for 4 days. The mixture was cooled to 0° C. after which Et3N (8.50 mL, 60.8 mmol) and methanesulfonyl chloride (5.88 mL, 76.0 mmol) were added. The mixture was stirred at 0° C. for 4 h. The reaction mixture was poured into a 1:1 mixture of saturated aqueous NaCl and water and was extracted with CH2Cl2. The organic layer was washed with saturated aqueous NaCl, dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography, elution with 0-50% EtOAc in heptane, to provide the title compound (5.88 g, 58%) as a white solid.

Provenance & Evidence