1.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 2.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 2.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 3.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 3.2: 39 mg / H2 / Pd/C / ethanol / 48 h 4.1: ethanol / 1.5 h / 0 °C 5.1: 24 mg / NaBH4 / ethanol / 0.67 h / 20 °C View Scheme

1.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 2.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 2.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 3.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 3.2: 39 mg / H2 / Pd/C / ethanol / 48 h 4.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

(S)-Alpine Hydride in tetrahydrofuran T=-78°C; 24 h;

1.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 2.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 2.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 3.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 3.2: 39 mg / H2 / Pd/C / ethanol / 48 h 4.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: 89 percent / pyridine / CH₂Cl₂ / 2 h / 20 &deg;C<br />2: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 &deg;C<br />3: 94 percent / EDCI / CH₂Cl₂ / 3.5 h / 0 &deg;C<br />4: 67 percent / t-BuOH; SmI₂ / tetrahydrofuran / 144 h / -78 &deg;C<br /> <br /> &nbsp;