1: With CoCl2.6H2O; (S)-p-Tol-BINAP in dichloromethane; N,N-dimethyl-formamide T=20°C; 1 h; Inert atmosphere; 2: With sodium tris(acetoxy)borohydride in dichloromethane; N,N-dimethyl-formamide T=20°C; Inert atmosphereCooling with ice; optical yield given as percent de;

1: NaBH(OAc)3; acetic acid / toluene / 16 h / 20 °C 2: LiAlH4 / tetrahydrofuran / 1 h / 20 °C 3: pyridine / CH2Cl2 4: 90 percent / H2 / Pd(OH)2/C / methanol / 50.4 h / 50 °C / 3102.89 Torr View Scheme

1: NaBH(OAc)3; acetic acid / toluene / 16 h / 20 °C 2: LiAlH4 / tetrahydrofuran / 1 h / 20 °C 3: pyridine / CH2Cl2 4: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 5: 100 percent / triethylamine / tetrahydrofuran / 1.5 h / -30 - -10 °C 6: 100 percent / H2 / Pd(OH)2/C / ethyl acetate / 16.5 h / 50 °C / 3102.89 Torr 7: 98 percent / K2CO3 / methanol; H2O / 16 h / 20 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: Et₃N; H₂ / Pd(OH)2/C / ethanol; H₂O / 0.42 h / 3102.89 Torr<br />2: toluene / 36 h / Heating<br /> <br /> &nbsp;