Water → HCID 178505327, compound

Participants

Reaction Steps

MsCl (0.27 mL, 3.5 mmol) was added dropwise to a solution of intermediate 40, cis-3-(Morpholin-4-ylmethyl)cyclobutanol (0.5 g, 2.9 mmol) and triethylamine (1 mL, 7.0 mmol) in CH2Cl2 (5 mL) in argon under stirring on an ice bath. The mixture was brought to room temperature for 1 h, water (10 mL) was added, and the layers were separated. The organic layer was washed with water. The water layer was washed with the saturated NaCl solution, dried over Na2SO4, and evaporated to give the title compound as a yellow oil in 99% (718 mg, 2.88 mmol) yield. This material was used without additional purification. 1H-NMR (400 MHz)-data (dmso-d6): 4.83 (dddd, 1H, J=7.5 Hz, CHOMs), 3.51-3.58 (m, 4H, CH2OCH2), 3.12 (s, 1H, Ms), 2.46-2.55 (m, 2H, cyclobutylCHH), 2.28-2.40 (m, 6H, (CH2)3N), 2.00-2.12 (m, 1H, CHCH2N), 1.80-1.89 (m, 2H, cyclobutylCHH).

Provenance & Evidence