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Reagents and conditions: (a) 1-hexyne or 1-dodecyne, Pd(PPh3)4, CuI, Et3N, 50 °C, 12 h; (b) Pd/C, H2, EtOAc; (c) (i) MsCl, Et3N, CH2Cl2; (ii) 4-hydroxypiperidine, MeCN, 50 °C, 12 h; (d) (i) MsCl, Et3N, CH2Cl2, 3 h, rt; (ii) NaN3, DMF, 80–100 °C, 12 h; (e) Pd/C, H2, CH2Cl2/MeOH (1:3), rt, 12 h.
