1: With peracetic acid in methanol; acetic acid T=0°C; 0.75 h; 2: With hydrogenchloride in water

1: With 3-chloro-benzenecarboperoxoic acid in ethyl acetate T=20°C; 24 h; 2: With hydrogenchloride in water; ethyl acetate

1: 1) NaH / 1) THF, r.t., 30 min, 2) THF, DMF, r.t., 90 min 2: 60 percent / NaBH4, CF3COOH / tetrahydrofuran / 20 h / ice bath cooling up to reflux 3: 1) CF3COOH, 2) 2-ethoxyethyl ether / 2) 10 percent Pd/C / 1) r.t., 30 min, 2) reflux, 6 h 4: 1) 32 percent peracetic acid, 2) aq. conc. HCl / 1) THF, 0 deg C, 20 min, 2) MeOH, 1 h View Scheme

1: 93 percent / K2CO3 / tetrahydrofuran / 2 h / Ambient temperature 2: 97 percent / AlH3 / tetrahydrofuran / 1.25 h / Ambient temperature 3: 99 percent / MnO2 / CHCl3 / 4 h / Heating 4: 1) CF3COOH, 2) 2-ethoxyethyl ether / 2) 10 percent Pd/C / 1) r.t., 30 min, 2) reflux, 6 h 5: 1) 32 percent peracetic acid, 2) aq. conc. HCl / 1) THF, 0 deg C, 20 min, 2) MeOH, 1 h View Scheme

1: 60 percent / NaBH4, CF3COOH / tetrahydrofuran / 20 h / ice bath cooling up to reflux 2: 1) CF3COOH, 2) 2-ethoxyethyl ether / 2) 10 percent Pd/C / 1) r.t., 30 min, 2) reflux, 6 h 3: 1) 32 percent peracetic acid, 2) aq. conc. HCl / 1) THF, 0 deg C, 20 min, 2) MeOH, 1 h View Scheme

hydrogenchloride in dichloromethane same prep. with Anion exchange resin (Dowex-1, chloride from) as reagent;

1: 1) NaH / 1) THF, r.t., 30 min, 2) THF, DMF, r.t., 90 min 2: 60 percent / NaBH4, CF3COOH / tetrahydrofuran / 20 h / ice bath cooling up to reflux 3: 1) CF3COOH, 2) 2-ethoxyethyl ether / 2) 10 percent Pd/C / 1) r.t., 30 min, 2) reflux, 6 h 4: 1) 32 percent peracetic acid, 2) aq. conc. HCl / 1) THF, 0 deg C, 20 min, 2) MeOH, 1 h View Scheme

3: 65 percent / toluene / 160 °C 4: LiOH / tetrahydrofuran; H2O / Ambient temperature 5: 80 percent / H2 / PtO2 / methanol 6: NaNO2 / aq. HCl; methanol / 0.75 h / 0 °C 7: aq. HCl; methanol / 1 h / Heating View Scheme

2: 65 percent / toluene / 160 °C 3: LiOH / tetrahydrofuran; H2O / Ambient temperature 4: 80 percent / H2 / PtO2 / methanol 5: NaNO2 / aq. HCl; methanol / 0.75 h / 0 °C 6: aq. HCl; methanol / 1 h / Heating View Scheme

1: 65 percent / toluene / 160 °C 2: LiOH / tetrahydrofuran; H2O / Ambient temperature 3: 80 percent / H2 / PtO2 / methanol 4: NaNO2 / aq. HCl; methanol / 0.75 h / 0 °C 5: aq. HCl; methanol / 1 h / Heating View Scheme