Scheme 14.
Methods used for the preparation of 23. Reagents and conditions: a) methyltriphenylphosphonium bromide, KOtBu, THF (81%); b) (i) BH3 TFA/DCM (79%); f) 20% Pd(OH)2/C, H2, ethanol (81%)THF, (ii) NaOH, H2O2 (77%); c) phthalimide PPh3, DIAD (91%); d) hydrazine monohydrate, methanol, reflux (74%); e) LiOH, THF; f) HOBT, EDC, DIPEA; g) 20% Pd(OH)2/C, H2, ethanol (97%); h) (i) BH3·THF, THF, (ii) Boc2O, DCM (49%); i) TFA, DCM (91%)