Water → HCID 86622336, compound

Participants

Reaction Steps

Step AE (2): To a solution of 2,2,2-trifluoro-N-((1R,2S)-2-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide in DMF (4.5 mL) at rt was added sodium hydride (95% purity, 205 mg). The resulting mixture was stirred at rt for 5 min. Allyl bromide (0.26 mL) was added, and the reaction mixture was stirred for 30 min. Water was added, the aqueous layer was extracted with EtOAc (×3), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give N-((1R,2S)-2-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide as a slightly yellowish oil (660 mg). 1H NMR (400 MHz, CDCl3) δ 7.14 (1H, d), 6.85 (1H, d), 6.83 (1H, s), 5.88 (1H, m), 5.44 (1H, d), 5.28 (1H, dt), 5.12 (1H, dt), 4.38 (1H, q), 4.06 (1H, m), 3.76 (3H, s), 3.05 (1H, d).

Provenance & Evidence