Scheme 2.
Synthesis of final compounds 34 and 35. Reagents and conditions: a) NaH (1.5 eq), alkyl iodide (1.5 eq), DMF, 0 °C to RT, overnight. b) Formaldehyde (2.0 eq), TFA (2.0 eq), amine (2.0 eq), DCM, 12h, RT. c) Aldehyde (1.2 eq), MeOH, N2 stream, RT, 12 h. Then, NaBH4 (3 eq), RT, 3h d) HOBt (1.2 eq), HBTU (1.2 eq), DIPEA (2.4 eq), L-Boc-Pra-OH (1.2 eq), DCM, 12h, RT.