tert-Butanol → HCID 44549666, compound

Participants

Reaction Steps

A suspension of acid 201 (2.08 g, 8.31 mmol) in dry t-BuOH (30 mL) containing powdered molecular sieves (1 g) was treated with Et3N (1.39 mL, 9.97 mmol) and stirred under N2 at room temperature for 30 min. DPPA (1.97 mL, 9.14 mmol) was added and the mixture was stirred at reflux for 7 h, then concentrated to half volume under reduced pressure and poured into dilute aqueous KHCO3. The resulting solid was purified by chromatography on silica gel, eluting with CH2Cl2/EtOAc (19:1), followed by recrystallization from CH2Cl2/iPr2O to give tert-butyl 7-(methylsulfonyl)-2-naphthylcarbamate (202) (2.11 g, 79%) as a white solid: mp 179-180° C.; 1H NMR [(CD3)2SO] δ 9.76 (s, 1H), 8.39 (d, J=1.5 Hz, 1H), 8.28 (d, J=1.5 Hz, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.98 (d, J=9.0 Hz, 1H), 7.77 (dd, J=8.6, 1.9 Hz, 1H), 7.74 (dd, J=9.2, 2.0 Hz, 1H), 3.27 (s, 3H), 1.52 (s, 9H). Anal. (C16H19NO4S) C, H, N.

Provenance & Evidence