Triphenylphosphine → HCID 86654476, compound

Participants

Reaction Steps

To a stirred solution of Ph3P (0.88 g, 3.35 mmol) and (±)-N-Boc-trans-3-(4-phenoxybenzenesulfonamido)-4-hydroxypyrrolidine (1.316 g, 3.04 mmol) in THF (20 mL) at 0° C. was added diethyl azodicarboxylate (DEAD) (0.58 mL, 3.33 mmol) dropwise. The reaction mixture was stirred at room temperature overnight, then it was evaporated under reduced pressure. The residue was purified by flash chromatography (30% ethyl acetate in hexane) to give the N-(4-phenoxybenzenesulfonyl)aziridine as a solid (1.23 g, 98%): mp 136-138° C.; 1H NMR (300 MHz, CDCl3) δ 7.88 (m, 2H), 7.43 (m, 2H), 7.22 (m, 1H), 7.10 (m, 4H), 3.72 (m, 2H), 3.59 (m, 1H), 3.47 (m, 1H), 3.38 (m, 2H), 1.42 (s, 9H); MS, ESI m/e 416.1 (M+); HRMS (ESI) calcd for C21H24N2O5SNa+ 439.1290. found 439.1290.

Provenance & Evidence