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. 2009 Sep 24;1(1):25–35. doi: 10.1021/cn900001b

Scheme 1.

Scheme 1

Reagents and conditions: (a) (1) propylamine, NaBH(OAc)3, THF, HOAc, RT, 1 h, reflux 18 h; (2) HCl in Et2O, Et2O; (b) 4-bromobutyronitrile, K2CO3, KI, CH3CN, reflux, 24 h; (c) LiAlH4 in Et2O, Et2O, RT, 1 h; (d) 4-biphenylcarboxylic acid chloride, Et3N, CH2Cl2, RT, 21 h; (e) ferrocene carboxylic acid, HATU, DIPEA, DMF, RT, 3 h; (f) [2.2]paracyclophane carboxylic acid, HATU, DIPEA, CH2Cl2, NMP, RT, 2.75−3 h; (g) propionaldehyde, NaBH(OAc)3, THF, HOAc, reflux 21 h.