Lithium iodide → HCID 59279488, compound

Participants

Reaction Conditions

Reaction Steps

Lithium iodide (1.986 g, 14.84 mmol) was added to (S)-methyl 2-(tert-butyldimethylsilyloxy)-3-cyclobutoxypropanoate (Intermediate R3) (1.07 g, 3.71 mmol) in ethyl acetate (15 mL). The resulting suspension was protected from light and stirred at reflux (75° C.) for 6 hours. The reaction mixture was diluted with ethyl acetate (75 mL) washed sequentially with 1M sodium metabisulphite (25 mL), water (25 mL) and saturated brine (25 mL). The organic layer was dried (MgSO4) and evaporated to afford the crude product (0.920 g, 90%) that was used without further purification. 1H NMR (400 MHz, DMSO) δ 0.09 (d, 6H), 0.91 (s, 9H), 1.40-1.54 (m, 1H), 1.59-1.71 (m, 1H), 1.75-1.90 (m, 2H), 2.10-2.22 (m, 2H), 3.40-3.57 (m, 2H), 3.90-4.02 (m, 1H), 4.25-4.31 (m, 1H), 12.55 (s, 1H); m/z (EI+) M+=274; GC tR=11.09 min.

Provenance & Evidence