Compound 71
6-phenyl-2-oxa-6-azaspiro[3.3]heptane
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 GP2 outlined for compound 45, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) at 0 °C, 2-oxa-6-azaspiro[3.3]heptane oxalate (2:1) (30 mg, 0.2 mmol) gave 71 (18 mg, 52%) as an oil. Rf 0.35 [petrol–EtOAc (95:5)]; FT-IR νmax (film)/cm–1 2969, 2853, 1319, 1291, 1157; 1H NMR (CDCl3, 400 MHz) δ 7.27–7.19 (2H, m), 6.77 (1H, t, J = 7.4 Hz), 6.47 (2H, dd, J = 8.5, 1.0 Hz), 3.96 (2H, s), 3.69 (2H, s), 3.72 (4H, ABq, JAB = 7.5 Hz); 13C NMR (CDCl3, 101 MHz) δ 151.2, 129.2, 118.0, 111.5, 64.7, 57.2, 47.9, 41.3; HRMS (APCI): Found MH+ 176.1073, C11H14NO requires 176.1070.
