Phenol → HCID 21077868, compound

Participants

Reaction Steps

A solution of diethyl azodicarboxylate (0.74 ml, 4.7 mmol) in anhydrous dichloromethane (3 ml) was added to a stirred, ice-methanol cooled solution of (RS)-1-(tert-butoxycarbonyl)-2-(2-hydroxyethyl) -4-methoxycarbonylpiperazine (D7) (1.35 g, 4.69 mmol), phenol (0.441 g, 4.69 mmol) and triphenylphosphine (1.23 g, 4.69 mmol) in anhydrous dichloromethane (40 ml). The mixture was stirred at room temperature for 18 h then evaporated in vacuo. The residue was chromatographed on silica gel eluting with 10-20% ethyl acetate in hexane to give the title compound (1.43 g, 84%). 1H NMR (CDC13) δ: 1.38 (9H, m), 1.85-2.20 (2H, m), 2.75-3.20 (3H, m), 3.72 (3H, s), 3.80-4.20 (5H, m), 4.39 (1H, broad m), 6.75-7.00 (3H, m), 7.15-7.35 (2H, m).

Provenance & Evidence