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. 2019 Jul 23;15:1722–1757. doi: 10.3762/bjoc.15.168

Scheme 18.

Scheme 18

Synthesis of pyrrolidine (3S,3'R)-68, a fragment of the fluoroquinolone antibiotic PF-00951966. Reagents and conditions: a) MeNO2, TBAF, THF, rt, 4 h; b) H2, 10% PtO2, MeOH, rt, 48 h; c) LiAlH4, THF, reflux, 1 h; d) Boc2O, EtOH, rt, 6 h; e) TfOMe, NaCN, MeCN, 0 °C to rt; f) H2, 10% Pd/C, Boc2O, THF, rt; g) CF3COOH, CH2Cl2, rt, 2 h.