Methanol → HCID 3027864, compound

Participants

Reaction Steps

To a solution of amine 90 (300 mg, 0.62 mmol) and Goodman's reagent (392 mg, 1.00 mmol) in MeOH (60 mL) was added DIPEA (0.45 mL, 2.5 mmol) at room temperature. The reaction mixture was stirred for 7 h and then concentrated. The residue was dissolved in CHCl3 (200 mL) and washed with saturated NaHCO3 (2×100 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, 90:9:1 CHCl3/CH3OH/NH4OH) to afford Boc-urea 92 (280 mg, 62%) as a light yellow solid: 1H NMR (300 MHz, CD3OD) δ 7.67 (t, J=7.8 Hz, 2H), 7.57 (s, 1H), 7.31 (d, J=8.1 Hz, 1H), 7.19 (s, 2H), 4.18 (t, J=5.4 Hz, 2H), 3.62 (t, J=6.0 Hz, 2H), 2.82 (t, J=6.3 Hz, 2H), 2.12 (t, J=5.7 Hz, 2H), 1.85-1.70 (m, 4H), 1.54 (s, 9H), 1.45 (s, 9H).

Provenance & Evidence