Water → (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

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Reaction Conditions

Reaction Steps

Ph3P (19.65 g, 75 mmol) was dissolved in 9:1 THF/CH3CN (600 mL) and cooled to 0° C., DIAD (14.7 mL, 75 mmol) was added dropwise over 15 min. After stirring for 30 min, a solution of (S)-2-(t-butoxycarbonylamino)-3-(t-butyldimethylsilyloxy)propan-1-ol (15.25 g, 50 mmol) in THF (100 mL) was added dropwise over 15 min, the reaction mixture was allowed to rt and stirred for 24 h. Water (100 mL) was added and volatiles were evaporated. The residue was partitioned between water (100 mL) and EtOAc (2×100 mL). The organic layers were washed with brine, dried over MgSO4 and evaporated. The residue was purified by silica chromatography to provide (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate (7.8 g, 54%) as an oil. 1H NMR (CDCl3, 400 MHz): δ 0.07 (s, 6H), 0.89 (s, 9H), 1.45 (s, 9H), 2.06 (d, J=3.6 Hz 1H), 2.26 (d, J=6 Hz 1H), 2.55 (m, 1H), 3.64 (dd, J=16.4, 4.8 Hz, 1H), 3.82 (dd, J=16.4, 4.4 Hz, 1H).

Provenance & Evidence