Water → 4-(((3-Fluoro)benzyloxy)methyl)benzylamine

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To a LiAlH4 (2.00 g, 53.4 mmol) suspension in THF (300 mL) was added dropwise a THF (20 mL) solution of 4-(((3-fluoro)benzyloxy)methyl)benzonitrile (4.30 g, 17.8 mmol) at 0° C. The mixture was stirred at room temperature (16 h) and H2O (1.6 mL) was added dropwise at 0° C. followed by an aqueous NaOH solution (0.8 mL, 15% w/w), and then H2O (1.6 mL). The mixture was stirred at room temperature (2 h), and the precipitate filtered and washed with CH2Cl2. The filtrate was concentrated in vacuo and the solid triturated with Et2O to obtain a white solid (1.60 g, 37%). The solid was used in the next step with no other purification: Rf=0.00 (hexanes/EtOAc 8/2); mp >138° C. (decomp.); IR (nujol) 3224, 3100, 3039, 2970, 2843, 1593, 1520, 1456, 1375, 1257, 1143, 1073, 940, 866, 733, 686, 549 cm−1; 1H NMR (CDCl3) δ 3.87 (s, CH2NH2), 4.47-4.54 (m, 2 CH2O), 7.08-7.45 (m, 8 ArH); 13C NMR (CDCl3) δ 43.1 (CH2N), 70.4, 71.2 (2 CH2O), 113.8 (d, J=21.7 Hz, C2′ or C4′), 114.1 (d, J=20.5 Hz, C4′ or C2′), 123.1 (d, J=2.3 Hz, C6′), 127.5 (ArC), 128.1 (ArC), 130.2 (d, J=8.0 Hz, C5′), 137.2, 137.3 (2 ArC), 141.4 (d, J=6.8 Hz, C1′), 162.1 (d, J=242.5 Hz, C3′); HRMS (M+H+) (ESI+) 246.1294 [M+H+] (calcd for C15H16FNOH+ 246.1294).

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