N-tosyl-(Sa)-binam-L-prolinamide; water; benzoic acid T=25°C; 48 h; Neat (no solvent); optical yield given as percent eeenantioselective reaction;

N-tosyl-(Sa)-binam-L-prolinamide; benzoic acid T=25°C; 48 h; Neat (no solvent); optical yield given as percent eeenantioselective reaction;

1: triethylamine / dichloromethane / 12 h 2: 4-nitro-benzoic acid; (S)-N-(2-(4-methylphenylsulfonamido)ethyl)pyrrolidine-2-carboxamide / acetonitrile / 96 h / -18 °C View Scheme

jones reagent Title compound not separated from byproducts.;

1: triethylamine / dichloromethane / 12 h 2: acetic acid / water / 48 h / 20 °C View Scheme

1: lithium tri-tert-butoxyaluminum hydride 2: 95.5 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 40 percent / 50percent NaH / dimethylsulfoxide / 1 h / Ambient temperature 4: H2 / 10percent Pd-C / ethanol / 26 h / 760 Torr 5: 97 percent / LiAlH4 / diethyl ether / 0.5 h / -30 °C 6: 1.) KH, 2.) n-BuLi / 1.) THF, 1.5 h, room temp., 2.) THF, hexane, -78 deg C, 2 h, -78 deg C -> room temp., 6 h 7: 100 percent / (i-Pr)2NEt / CH2Cl2 / 0.33 h / Ambient temperature 8: 1.) 1 M BH3*THF, 2.) 3 M NaOH, 40percent H2O2 / 1.) 2-methoxyethyl ether, room temp., 24 h, 2.) THF, water, 50 deg C, 1 h 9: 100 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h 10: 348 mg / NaOCH3 / methanol / 9.5 h / Heating 11: 36.8 percent / benzene / 9.5 h / Irradiation 12: 81.2 percent / tetra-n-butylammonium fluoride trihydrate / bis-(2-methoxy-ethyl) ether / 36 h / 55 °C / 2 Torr 13: 80.5 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature 14: 1.) tetra-n-butylammonium fluoride, 2.) Pd(OAc)2 / 1.) THF, 30 min, 2.) CH3CN, 33.5 h 15: 97 percent / CeCl3*7H2O, NaBH4 / methanol / 0.33 h / 0 °C 16: 62.4 percent / diethyl azodicarboxylate, Ph3P / benzene / 3 h / Ambient temperature 17: 61 percent / 35percent HClO4 / tetrahydrofuran; H2O / 25 h 18: 77 percent / 5percent potassium hydroxide / ethanol / 3 h / 50 °C View Scheme