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. 2020 Dec 3;16(5):860–868. doi: 10.1002/cmdc.202000814

Scheme 1.

Scheme 1

Synthesis of new bis‐3‐chloropiperidine derivatives 6 and 8. a) Boc2O, 1 M NaOH, H2O/dioxane (1 : 1), RT, 12 h; b) ClCO2Et, NEt3, benzyl amine, dioxane, RT, 12 h; c) TFA, CH2Cl2, 0 °C to RT, 3 h; d) 2,2‐dimethoxypropane, conc. HCl, MeOH, reflux to RT, 15 h; e) 2,2‐dimethylpent‐4‐enal, [5] NaBH(OAc)3, AcOH, dry CH2Cl2, 0 °C to RT, 12 h; f) NCS, dry CH2Cl2, 0 °C to RT, 2.5–3.5 h; g) cat. TBAI, dry CHCl3, 60 °C (oil bath temperature), 2 h, (inseparable diastereomeric mixture).