Water → HCID 69320996, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (3R)-3-ethyl-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (0.250 g, 0.734 mmol) and K2CO3 (0.507 g, 3.67 mmol) in 3 mL DMF was added allyl bromide (0.636 mL, 7.34 mmol) and the reaction mixture was heated to 50° C. for 4 h. The reaction mixture was poured into 40 mL water and extracted with EtOAc (2×30 mL). The extracts were washed with 40 mL each water and brine, dried over MgSO4, filtered and concentrated to a yellow oil. Column chromatography (5–10% EtOAc in hexane gradient) afforded 0.24 g (86% yield) of (3R)-4-allyl-3-ethyl-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline, a yellow oil. Rf0.6 (9:1 hexane:EtOAc); 1H NMR (400 MHz, CDCl3) δ7.41 (d, 1H, J=9.0), 7.21 (d, 1H, J=9.0), 7.18 (s, 1H), 5.96–5.85 (m, 1H), 5.47 (septet, 1H, J=6.1), 5.25 (dd, ABX, 1H, J=17.1, 1.1), 5.20 (d, 1H, J=10.1), 4.31 (dd, ABX, 1H, J=10.7, 2.2), 4.03 (dd, ABX, 1H, J=16.8, 5.0), 3.95–3.89 (m, 2H), 3.27–3.22 (m, 1H), 1.69–1.59 (m, 2H), 1.38 (d, 3H, J=6.1), 1.37 (d, 3H, J=6.1), 0.97 (t, 3H, J=7.5).

Provenance & Evidence