4-Toluenesulfonyl chloride → Tert-butyl 2-methylaziridine-1-carboxylate

Participants

Reaction Steps

To a solution of (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate (756 mg, 4.31 mmol) and 4-methylbenzene-1-sulfonyl chloride (905 mg, 4.75 mmol) in ethyl ether (30 mL) was added powdered potassium hydroxide (968 mg, 17.26 mmol) and reaction was refluxed for 2 hr. The reaction mixture was poured into a separatory funnel that contained crushed ice and extracted with ether (2×20 mL). The organics were combined, dried with sodium sulfate, filtered, and concentrated. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.16 (d, J=5.43 Hz, 3H) 1.38 (s, 9H) 1.83 (d, J=3.73 Hz, 1H) 2.17 (d, J=5.76 Hz, 1H) 2.40 (qd, J=5.65, 3.73 Hz, 1H).

Provenance & Evidence