1: With 4-methyl-morpholine; isobutyl chloroformate in ethylene glycol dimethyl ether T=-15°C; 0.166667 h; 2: With sodium tetrahydroborate; water in ethylene glycol dimethyl ether T=-15°C; 0.0833333 h;

palladium dihydroxide; hydrogen in tetrahydrofuran P=3800.26 Torr; 48 h;

1: 85 percent / 1,3-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 2 h / 20 °C 2: 100 percent / H2 / Pd/C / ethanol / 1 h / 2585.74 Torr 3: 80 percent / BH3*THF / tetrahydrofuran / 1 h / -15 °C View Scheme

1: 100 percent / H2 / Pd/C / ethanol / 1 h / 2585.74 Torr 2: 80 percent / BH3*THF / tetrahydrofuran / 1 h / -15 °C View Scheme

Multistep reaction. Title compound not separated from byproducts.;

1: 1.24 g / oxalyl chloride, DMSO, Et3N / CH2Cl2 / -78 deg C, 0.5 h, 0 deg C, 2 h 2: 87 percent / NaBH3CN / methanol; tetrahydrofuran / 20 h / 0 °C 3: trimethylsilyl triflate / CH2Cl2 / 0.5 h / 0 °C 4: AcOH / methanol 5: NaBH3CN / tetrahydrofuran; methanol / 19.5 h / 0 °C 6: HCl, anisole / H2O; tetrahydrofuran / 17 h / Ambient temperature View Scheme

1: 95 percent / polymer-bound-NMe3(1+)*Br(OAc)2-; TEMPO / CH2Cl2 / 16 h / 20 °C 2: 15 percent / NaOEt / ethanol / 12 h / 20 °C 3: ammonium formate / Pd/C / methanol / 2 h / -10 °C 4: 3.3 g / N,N-diisopropylamine / dimethylformamide / 16 h / 20 °C View Scheme