8-Quinolinesulfonyl chloride → (R)-4-Allyl-5-(quinolin-8-ylsulfonyl)-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocine

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Reaction Steps

A solution of compound 18l (1.2 g, 5.9 mmol), quinoline-8-sulfonyl chloride (1.5 g, 6.5 mmol), TEA (1.8 g, 17.7 mmol) and DMAP (366 mg, 3 mmol) in 20 mL of DCM was stirred at rt overnight. The mixture was concentrated and the residue was purified by CC to give the desired compound 18 (1.3 g, 56% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.94 (m, 1H), 8.46 (d, J=7.5 Hz, 1H), 8.13 (d, J=8.5 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.54 (t, J=8.0 Hz, 1H), 7.43 (dd, J=4.0, 8.0 Hz, 1H), 7.20 (d, J=7.5 Hz, 1H), 6.98 (m, 1H), 6.91 (m, 1H), 6.80 (d, J=7.5 Hz, 1H), 5.69 (m, 1H), 5.07-4.86 (m, 5H), 4.58 (d, J=15.0 Hz, 1H), 4.54 (m, 1H), 4.01 (d, J=12.5 Hz, 1H), 3.68 (d, J=12.5 Hz, 1H), 2.47 (m, 1H), 2.09 (m, 1H). LCMS (m/z): 395.5 (MH+).

Provenance & Evidence