Compound 94
2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-dextromethorphan
From: Practical and regioselective amination of arenes using alkyl amines
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Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP1 outlined for compound 4, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) but using 1.0 equiv. of dextromethorphan, (27 mg, 0.1 mmol) (as solution in HFIP 0.5 mL), 1.2 equiv. 2-oxa-6-azaspiro[3.3]heptane oxalate (2:1), 1.2 equiv.of NCS, 1.4 of equiv of N,N-diisopropylehtylamine and 6.0 equiv. of HClO4, gave 94 (16 mg, 42%) as an oil. Rf 0.25 [DCM–MeOH–NEt3 (0.95:0.05:0.01)]. FT-IR νmax (film)/cm–1 2916, 2898, 2786, 1498, 1441, 1287, 1156, 1098; 1H NMR (500 MHz, CDCl3) δ 6.61 (1H, s), 6.14 (1H, s), 3.94 (2H, s), 3.91 (2H, s), 3.76 (2H, t, J=7.5 Hz), 3.73 (3H, s), 3.70 (2H, dd, J=7.8, 5.7 Hz), 2.89 (1H, d, J=18.2 Hz), 2.82 – 2.76 (1H, m), 2.55 (1H, ABq, JAB = 18.2, 5.8 Hz), 2.46 – 2.39 (1H, m), 2.39 (3H, s), 2.27 (1H, d, J=12.5 Hz), 2.10 (1H, td, J=12.2, 3.1 Hz), 1.79 (1H, d, J=12.5 Hz), 1.70 (1H, td, J=12.6, 4.7 Hz), 1.62 (1H, d, J=11.8 Hz), 1.50 (1H, d, J=11.0 Hz), 1.40 – 1.23 (5H, m), 1.17 – 1.09 (1H, m); 13C NMR (125 MHz, CDCl3) δ 148.4, 138.3, 131.0, 129.9, 112.1, 108.4, 64.5, 58.7, 58.7, 58.3, 55.8, 48.3, 47.5, 45.4, 42.8, 42.0, 41.7, 36.9, 36.7, 26.7, 26.7, 23.9, 22.4; HRMS (APCI): Found MH+ 368.271, C23H33N2O2 requires 368.2465.
