Propargyl-choline synthesis

Propargyl-choline (Pro-Cho) was synthesized using the method described [³³]. Briefly, dimethylethanolamine (3.54 ml, 35.3 mmol; Sigma Aldrich, 38,990) was added to a solution of propargyl bromide (80% in toluene, 3.74 ml, 33.6 mmol; Sigma Aldrich, 81,831) in anhydrous tetrahydrofuran (THF; 10 ml; VWR, 44,608.AE) at 0°C under a nitrogen atmosphere. The solution was allowed to warm to room temperature and was stirred for 18 h, after which time the resultant solid was washed with cold THF (3 x 20 ml) and dried in vacuo to afford the title compound as an off-white solid (6.05 g, 87% yield).

The sample was analyzed by ¹H NMR (in MeOD): 4.87 (1H, s), 4.46 (2H, d, J = 2.3 Hz), 4.04 (2H, a-dq, J = 2.5, 4.8 Hz), 3.62 (2H, m), 3.56 (1H, t, J = 2.5 Hz), 3.29 (6H, s); ¹³C NMR (in MeOD): 81.3 (C, t, J = 40 Hz), 70.7 (CH, t, 8 Hz), 65.3 (CH₂, s), 55.5 (CH₂, s), 55.0 (CH₂, s), 50.6 (CH₃x2, s).