1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 1.2: -98 - -78 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux 3.1: water; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C View Scheme

1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 1.2: -98 - -78 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1.1: triethylamine / dichloromethane / 15 h / 20 &deg;C / Inert atmosphere<br />2.1: (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 20 &deg;C / Inert atmosphere<br />2.2: 16 h / 5 &deg;C / Inert atmosphere<br />3.1: platinum(IV) oxide; hydrogen / ethyl acetate / 15 h / 760.05 Torr<br />4.1: triethylamine / dichloromethane / 144 h / Inert atmosphere; Reflux<br /> <br /> &nbsp;