(Diethylamino)sulfur trifluoride → HCID 68291692, compound

Participants

Reaction Steps

DAST (2.99 ml, 22.60 mmol) was added dropwise to a stirred solution of (R)-1-(1-(dibenzylamino)ethyl)cyclopropanol (5.3 g, 18.83 mmol) in dichloromethane (94 ml) at −78° C. under a nitrogen atmosphere. The reaction was allowed to stir for about 2 hrs before quenching with sat. sodium bicarbonate solution (100 mL) via dropwise addition. The quenched reaction was allowed to warm slowly to rt overnight. The organic layer was separated, dried (MgSO4) and evaporated in vacuo before purifying by column chromatography using hexane to 2% ethyl acetate in hexane as eluent to give the title compound (1.16 g, 4.09 mmol, 21.73% yield). HPLC (condition B): retention time=3.69 min. LCMS (condition B): m/z 284.2. 1H NMR (400 MHz, MeOD) δ ppm 7.11-7.52 (10 H, m), 4.98-5.32 (1 H, m), 3.76-4.08 (4 H, m), 1.08-1.42 (3 H, m), 0.47-0.82 (4 H, m).

Provenance & Evidence