1: 80 percent / H2 / PtO2 / ethyl acetate / 1.25 h / 2068.6 Torr 2: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu2O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h 3: 87 percent / K2CO3 / dimethylformamide / Ambient temperature 4: 70 percent / aq. NaOH / methanol / 2 h / Heating View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: 100 percent / NaBH₄ / methanol; tetrahydrofuran / 2 h / 0 &deg;C<br />2: 95 percent / Et₃SiH, TFA / 1.) 0 deg C, 1.5 h, 2.) RT, overnight<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 85 percent / diisopropylethylamine / dimethylformamide / 3 h / 91 - 94 &deg;C<br />2: 100 percent / NaBH₄ / methanol; tetrahydrofuran / 2 h / 0 &deg;C<br />3: 95 percent / Et₃SiH, TFA / 1.) 0 deg C, 1.5 h, 2.) RT, overnight<br /> <br /> &nbsp;