tert-Butanol → HCID 44549528, compound

Participants

Reaction Steps

A suspension of acid 160 (4.08 g, 16.30 mmol) in dry t-BuOH (70 mL) containing powdered molecular sieves (2 g) was treated with Et3N (2.73 mL, 19.59 mmol) and stirred under N2 at room temperature for 30 min. DPPA (3.87 mL, 17.96 mmol) was added and the mixture was stirred at reflux for 6 h, then concentrated to a small volume under reduced pressure and poured into dilute aqueous NaHCO3. The resulting solid was purified by chromatography on silica gel, eluting with CH2Cl2, to give tert-butyl 6-(methylsulfonyl)-2-naphthylcarbamate (161) (4.57 g, 87%) as a white solid: mp (EtOAc/hexane) 203-204° C.; 1H NMR [(CD3)2SO] δ 9.81 (s, 1H); 8.44 (d, J=1.2 Hz, 1H), 8.26 (s, 1H), 8.08 (d, J=9.0 Hz, 1H), 8.01 (d, J=8.7 Hz, 1H), 7.84 (dd, J=8.7, 1.8 Hz, 1H), 7.66 (dd, J=8.9, 2.0 Hz, 1H), 3.25 (s, 3H), 1.52 (s, 9H). Anal. (C16H19NO4S) Cl, N.

Provenance & Evidence