Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68674598, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.91 g (3.5 mmol) of (±)-tert-butyl 2-[(isobutyl {[9-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl]methyl}amino)carbonyl]morpholine-4-carboxylate and 0.088 g (0.35 mmol, 0.1 equiv) of pyridinium p-toluenesulfonate in 25 mL of ethanol was stirred under nitrogen at 55° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (10-50% ethyl acetate in hexanes) to give the product as a solid white foam. MS (m+1)=461.4; H NMR (400 MHz, CDCl3) 7.29 (m, 1H), 7.05 (m, 1H), 6.96 (m, 1H), 4.91 (t, 1H, J 8 Hz), 4.75 (m, 1H), 4.48 (d, 1H, J 16 Hz), 4.18-4.02 (m, 2H), 4.01-3.80 (m, 2H), 3.57-3.38 (m, 2H), 3.21 (m, 1H), 3.10-2.85 (m, 3H), 2.69 (m, 1H), 2.01 (m, 3H), 1.78 (m, 3H), 1.57 (m, 2H, obscured by H2O peak), 1.45 (d, 9H, J 15 Hz), 0.90 (m, 6H).

Provenance & Evidence