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.