Reaction #306658

Reaction equation

Example 34b

1-[2-(2-Bromo-ethoxy)-5-chloro-4-methoxy-6-methyl-3-(3-phenyl-propoxy)-phenyl]-ethanone

3-hydroxyazetidine hydrochloride

→

title compound

Yield 16.0%

1-[3-Chloro-6-[2-(3-hydroxy-azetidin-1-yl)-ethoxy]-4-methoxy-2-methyl-5-(3-phenyl-propoxy)-phenyl]-ethanone

Yield 16.0%

Conditions

Workup

1. 1
   Otherthe crude product was purified by flash chromatography (silica gel, hexane/Et2O 1:1)

Procedure

Example 34b (207 mg, 0.46 mmol), CsCO3 (2.48 eq.) and 3-hydroxyazetidine hydrochloride (1.4 eq.) were reacted as described under General Procedure L and the crude product was purified by flash chromatography (silica gel, hexane/Et2O 1:1) to afford the title compound as a pale yellow oil (34 mg, 16%). 1H NMR (300 MHz, CDCl3) δ 7.33-7.20 (m, 5H), 4.40 (quintet, J=5.7 Hz, 1H), 4.07 (t, J=6.5 Hz, 2H), 3.98 (t, J=5.7 Hz, 2H), 3.88 (s, 3H), 3.67-3.62 (m, 2H), 2.96-2.91 (m, 2H), 2.85-2.80 (m, 2H), 2.73 (t, J=5.7 Hz, 2H), 2.51 (s, 3H), 2.19 (s, 3H), 2.13-2.03 (m, 2H). MS (ES+) m/z 448.2 (M+H+).

Source