Triethylamine → HCID 90411842, compound

Participants

Reaction Steps

A mixture of Example 304A (0.100 g, 0.225 mmol), (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (0.141 g, 0.270 mmol), triethylamine (0.157 mL, 1.126 mmol), and azetidin-3-ol.hydrochloride (0.030 g, 0.270 mmol) in N,N-dimethylformamide (2.5 mL) was stirred for 3 hours. The mixture was treated with water and brine and extracted with ethyl acetate (twice). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel using the ISCO Companion flash system eluting with dichloromethane/methanol/ammonium hydroxide (18:1:0.1 to 12:1:0.1) to give the title compound. 1H NMR (500 MHz, Methanol-d4) δ 1.60-1.70 (m, 1H), 1.91-1.99 (m, 1H), 2.06-2.17 (m, 2H), 2.16-2.27 (m, 1H), 2.82-2.91 (m, 1H), 3.26-3.34 (m, 1H), 3.51-3.58 (m, 1H), 3.63-3.70 (m, 1H), 3.76-3.78 (m, 4H), 4.00 (td, J=9.9, 4.3 Hz, 1H), 4.21 (dd, J=10.6, 6.9 Hz, 1H), 4.33-4.46 (m, 1H), 4.49-4.69 (m, 2H), 6.23 (s, 1H), 6.48-6.53 (m, 1H), 7.07 (d, J=5.1 Hz, 1H), 7.09-7.20 (m, 3H), 8.15 (d, J=5.1 Hz, 1H). MS (ESI+) m/z 463.1 (M+H)+.

Provenance & Evidence