hydrogen; acetic acid; palladium dihydroxide in methanol P=2585.7 Torr; 2 h;

1: 64 percent / potassium bis-trimethylsilylamide, Davis's oxaziridine = Ph-C(O)-N-SO2Ph / tetrahydrofuran; toluene / 0.5 h / -100 - -91 °C 2: 1) trifluoroacetic anhydride, dimethylsulphoxide, 2) ethyldiisopropylamine / 1) CH2Cl2, -78 deg C, 30 min, 2) 45 min 3: 78 percent 4: 1) hydrogen, acetic acid, 2) potassium carbonate / 1) platinum(VI) oxide / 1) ethyl acetate, 1 atm, 14 h, 2) methanol, 3 h 5: 90 percent / hydrogen, acetic acid / Pd(OH)2 / C / methanol / 2 h / 2585.7 Torr View Scheme

1: 1) trifluoroacetic anhydride, dimethylsulphoxide, 2) ethyldiisopropylamine / 1) CH2Cl2, -78 deg C, 30 min, 2) 45 min 2: 78 percent 3: 1) hydrogen, acetic acid, 2) potassium carbonate / 1) platinum(VI) oxide / 1) ethyl acetate, 1 atm, 14 h, 2) methanol, 3 h 4: 90 percent / hydrogen, acetic acid / Pd(OH)2 / C / methanol / 2 h / 2585.7 Torr View Scheme

1: 78 percent 2: 1) hydrogen, acetic acid, 2) potassium carbonate / 1) platinum(VI) oxide / 1) ethyl acetate, 1 atm, 14 h, 2) methanol, 3 h 3: 90 percent / hydrogen, acetic acid / Pd(OH)2 / C / methanol / 2 h / 2585.7 Torr View Scheme

1: 1) hydrogen, acetic acid, 2) potassium carbonate / 1) platinum(VI) oxide / 1) ethyl acetate, 1 atm, 14 h, 2) methanol, 3 h 2: 90 percent / hydrogen, acetic acid / Pd(OH)2 / C / methanol / 2 h / 2585.7 Torr View Scheme

hydrogen; palladium dihydroxide in methanol 1.75 h; Ambient temperature; Yield given;

1: 99 percent / CBr4, PPh3 / CH2Cl2 / 1.5 h / 0 °C 2: 78 percent / K2CO3, KI / dimethylformamide / 55 h / Ambient temperature 3: 64 percent / TFA / 3 h / Ambient temperature 4: H2 / Pd(OH)2 / methanol / 1.75 h / Ambient temperature View Scheme

1: 78 percent / K2CO3, KI / dimethylformamide / 55 h / Ambient temperature 2: 64 percent / TFA / 3 h / Ambient temperature 3: H2 / Pd(OH)2 / methanol / 1.75 h / Ambient temperature View Scheme

1: Et3N 2: NaCNBH3, HCl 3: NaOMe / methanol 4: N-phenylsulfonyl-3-phenyloxaziridine, KN(SiMe3)2 / toluene / -90 °C 5: Me2SO 6: i-Pr2NEt 7: methanol / 55 °C 8: H2 / Pt 9: K2CO3 10: H2 / Pd(OH)2 View Scheme

1: Dowex 50W-X8 (H+ form) / acetone 2: Et3N 3: NaCNBH3, HCl 4: NaOMe / methanol 5: N-phenylsulfonyl-3-phenyloxaziridine, KN(SiMe3)2 / toluene / -90 °C 6: Me2SO 7: i-Pr2NEt 8: methanol / 55 °C 9: H2 / Pt 10: K2CO3 11: H2 / Pd(OH)2 View Scheme