Allyl bromide → HCID 86622327, compound

Participants

Reaction Steps

Step Z (5). A solution of 1.7 g (5.25 mmol) of N-((1S,3R)-6-bromo-3-hydroxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide from step Z (4) was dissolved in 30 mL of DMF, and a suspension of 60% NaH in mineral oil (630 mg, 15.75 mmol) was added in portions to minimize gas evolution. The resulting reaction mixture was stirred at rt for 10 min, and then allyl bromide (953 mg, 7.8 mmol) was added. After stirring at rt for 3 h, the starting material was consumed. The reaction solution was diluted with 60 mL of ether and the remaining NaH was slowly quenched with water. Brine (20 mL) was then added, and the organic layer was removed followed by extraction of the aqueous layer with 2 more portions of ether. The combined organics were dried and concentrated, and the crude product was purified by chromatography eluting with a gradient of 0 to 15% EtOAc in hexanes to provide 1.26 g (74% yield) of N-((1S,3R)-3-(allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide. 1H NMR (500 MHz, CDCl3) δ ppm 2.06 (ddd, J=13.89, 3.05, 2.90 Hz, 1H) 2.70 (ddd, J=13.89, 7.17, 5.49 Hz, 1H) 4.07 (ddd, J=5.65, 1.53, 1.37 Hz, 2H) 4.80 (dd, J=5.65, 2.59 Hz, 1H) 5.22 (dd, J=10.38, 1.22 Hz, 1H) 5.29 (ddd, J=17.32, 3.13, 1.53 Hz, 1H) 5.37-5.44 (m, 1H) 5.84-5.95 (m, 1H) 6.81 (d, J=7.63 Hz, 1H) 7.30 (d, J=7.93 Hz, 1H) 7.49 (dd, J=7.93, 1.83 Hz, 1H) 7.58 (d, J=1.53 Hz, 1H).

Provenance & Evidence