Compound 11b
4-(5-Phenyl-1,4-oxazepan-3-yl)benzonitrile
From: SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes
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InChIKey JXJCMEBPAIJJDR-ZWKOTPCHSA-N
Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Compound 11b was synthesized by the general method outlined for compound 10a, replacing SnAP reagent 1 with 2. Purification by flash column chromatography (cyclohexane/EtOAc 7:1) afforded 11b (103 mg, 74% yield, d.r. = 9:1) as clear, colorless solid. IR (thin film): ν 2940, 2857, 2227, 1607, 1131 cm-1; 1H NMR (400 MHz, CDCl3): δ 7.65-7.57 (m, 2H), 7.56-7.52 (m, 2H), 7.44-7.39 (m, 2H), 7.36-7.30 (m, 2H), 7.28-7.23 (m, 1H), 4.21 (dd, J = 9.5, 3.2 Hz, 1H), 4.17 (dd, J = 9.5, 3.9 Hz, 1H), 4.07-3.90 (m, 3H), 3.60 (dd, J = 12.3, 9.5 Hz, 1H), 2.31-2.11 (m, 2H), 1.77 (br s, NH); 13C NMR (100 MHz, CDCl3): δ 146.7, 145.9, 132.5, 128.9, 128.2, 127.5, 126.6, 118.9, 111.6, 78.2, 69.1, 65.7, 62.2, 40.9; m.p. = 114–117 °C; ESI-HRMS calcd for C18H19N2O1 [M + H] 279.1492, found 279.1494.
