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Reagents and conditions: (a) HCl in p-dioxane, RT, 30 min, ~100%. (b) for 3a: ethyl 4-bromobutanoate, toluene, 120°C, 2 h, 65%; for 3b: t-Bu 4-iodobutanoate, K2CO3, ACN, RT, 3 d, 80%. (c) for 4a: neat ethyl 4-iodobutanoate, 115°C, 16 h, 95%; for 4b: t-Bu 4-iodobutanoate, ACN, RT, 13 d, 50%. (d) for 5a: conc. HCl, gla. HOAc, 100°C, 2 d, 91%; for 5b: HCl in p-dioxane, DCM, RT, 41 h, 67%. (e) N, N′-disuccinimidyl carbonate, pyridine, ACN, 50 – 60°C, 16 – 64 h, 37 – 64%.
