1: 85 percent / t-BuOK / acetonitrile / 12 h / 20 °C 2: 100 percent / TBAF / acetonitrile / 4 h / 20 °C 3: 79 percent / TEMPO; NaClO; NaClO2 / acetonitrile; aq. phosphate buffer / 4 h / 55 °C View Scheme

1: 85 percent / t-BuOK / acetonitrile / 12 h / 20 °C 2: 100 percent / TBAF / acetonitrile / 4 h / 20 °C View Scheme

1: 97 percent / DIAD; Ph3P / tetrahydrofuran / -20 - 20 °C 2: 85 percent / LiBEt3H / tetrahydrofuran; diethyl ether / 1.5 h / -50 °C 3: 99 percent / TBAF*3H2O / acetonitrile View Scheme

Multi-step reaction with 2 steps 1: 97 percent / DIAD; Ph3P / tetrahydrofuran / -20 - 20 °C2: 85 percent / LiBEt3H / tetrahydrofuran; diethyl ether / 1.5 h / -50 °C  

With  diisobutylaluminium hydride; (S)-1-methyl-2-lt;(piperidin-1-yl)-methylgt;pyrrolidine; tin(ll) chloride in  dichloromethane T=-100°C; 0.333333 h;  Yield given. Title compound not separated from byproducts;   

Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C2.1: tetrabutyl ammonium fluoride / acetonitrile3.1: sodium hydride / tetrahydrofuran / 1 h3.2: |Darkness4.1: hydrogenchloride / tetrahydrofuran; water / 4 h  

With  diisobutylaluminium hydride; (S)-1-methyl-2-lt;(piperidin-1-yl)-methylgt;pyrrolidine; tin(ll) chloride in  dichloromethane T=-100°C; 0.333333 h;  Yield given. Title compound not separated from byproducts;