Tetrahydrofuran → HCID 87176143, compound

Reaction equation

[CH3:1][CH:2]1[CH:10]([NH2:11])[CH2:9][CH:5]2[C:6]([CH3:8])([CH3:7])[CH:3]1[CH2:4]2.[CH2:12]1[CH2:18][S:15](=[O:17])(=[O:16])[O:14][CH2:13]1.O1CCC[CH2:20]1>O>[CH3:20][C@:3]12[CH2:4][C@H:5]([C:6]1([CH3:7])[CH3:8])[CH2:9][C@@H:10]([NH:11][CH2:13][CH2:12][CH2:18][S:15]([OH:14])(=[O:17])=[O:16])[C@@H:2]2[CH3:1]

Participants

Procedure

To a solution of (1R,2R,3R,5S)-(−)-isopinocampheylamine (2.0 g, 13.0 mmol) in tetrahydrofuran (20 mL) was slowly added 1,3-propanesultone (1.56 g, 12.5 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid product was collected by filtration, washed with acetone (2×25 mL), and dried in a vacuum oven (50° C.), to afford compound EH (2.7 g, 80%). 1H NMR (DMSO, 500 MHz) δ ppm 3.32 (m, 2H), 3.09 (d, 2H), 2.67 (m, 2H), 2.30 (m, 2H), 1.96 (m, 4H), 1.75 (m, 2H), 1.18 (s, 3H), 1.11 (m, 4H), 0.90 (s, 3H). 13C NMR (DMSO, 125 MHz) δ ppm 55.97, 50.11, 47.55, 45.86, 41.15, 40.91, 38.94, 32.81, 31.61, 27.96, 23.85, 22.59, 21.21, [α]D=−17.2° (c=0.00083 in water), ES-MS 274 (M−1).