Compound 36

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InChIKey GDVIDOQNFNLJNP-BGQGMAKMSA-N

Compound data: NMR

Compound data: Crystallographic data

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Potassium carbonate (19 mg, 0.14 mmol, 4.00 eq.) was charged in a flame-dried vial under an atmosphere of nitrogen. A solution of diamine 35 (11 mg, 0.04 mmol, 1.00 eq.) in anhydrous acetonitrile (0.2 mL) was added, followed by benzyl bromide (17 µL, 0.14 mmol, 4.00 eq.). The vial was capped and the white suspension was stirred at 80 °C for 18 h. The reaction mixture was allowed to cool to room temperature, diluted with water (1 mL) and extracted with Et₂O (3 × 1 mL). The organic layers were combined, washed with brine, dried over MgSO₄, filtered and concentrated. The residue was purified by flash column chromatography (n-pentane:Et₂O 99:1) to give diamine 36 (15 mg, 64%) as a colourless liquid. . TLC: R_f = 0.67 (n-pentane:Et₂O 90:10). ¹H NMR (500 MHz, Chloroform-d): δ 7.37 (8H, m, H3), 7.29 (8H, m, H2), 7.19 (4H, m, H1), 3.73 (4H, d, J = 13.6 Hz, H5), 3.26 (4H, d, J = 13.6 Hz, H5’), 2.48 (2H, dq, J = 10.0, 6.5 Hz, H6), 2.04 (2H, dqd, J = 9.9, 6.8, 2.4 Hz, H10), 1.73 (2H, dqd, J = 10.0, 6.8, 2.4 Hz, H8), 1.42 – 1.33 (4H, m, H12 & H14), 1.01 (6H, d, J = 6.5 Hz, H7), 0.63 (6H, d, J = 6.8 Hz, H13), 0.57 (6H, d, J = 6.8 Hz, H9), 0.56 (6H, m, H15), 0.22 (6H, d, J = 6.8 Hz, H11) ppm. ¹³C NMR (126 MHz, Chloroform-d): δ 140.5 (C4), 129.2 (C3), 128.1 (C2), 126.8 (C1), 54.8 (C6), 53.7 (C5), 36.5 (C8), 36.0 (C12 or C14), 35.4 (C14 or C12), 34.4 (C10), 12.5 (C9 or C15), 12.2 (C13), 11.7 (C11), 11.6 (C15 or C9), 9.9 (C7) ppm. HRMS (m/z): (MALDI⁺) calc’d. for C₄₈H₆₈N₂Na [M+Na]⁺: 695.5275; found 695.5282. IR (ν_max): 3085, 3063, 3027, 2968, 2929, 2876, 2801, 1945, 1873, 1801, 1740, 1603, 1494, 1453, 1381, 1028, 744, 730, 697 cm⁻¹. [α]_D²⁴: +11 (CHCl₃, c = 1.0).