hydrogenchloride; acetyl chloride 72 h;

1: methanol; acetyl chloride T=0°C; 0.75 h; 2: (3R)-1-[(1S)-1-phenylethyl]-3-pyrrolidineacetonitrile in methanol T=0 - 20°C; 100 h; 3: With water in methanol 0.75 h;

in methanol T=0 - 20°C; 100 h;

borane-THF in tetrahydrofuran 1 h; Heating;

T=20°C; 100 h;

1: 78 percent / triethylamine, N,N-dimethylaminopyridine / CH2Cl2 / 1 h / 0 °C 2: 1.) NaH, 2.) NaOH 3: 75 percent / aq. sodium chloride / dimethylformamide / 3 h / Heating 4: 1.) BH3*THF, 2.) HCl / 1.) reflux, 1 h, 2.) MeOH, reflux, 1 h View Scheme

1: 1.) NaH, 2.) NaOH 2: 75 percent / aq. sodium chloride / dimethylformamide / 3 h / Heating 3: 1.) BH3*THF, 2.) HCl / 1.) reflux, 1 h, 2.) MeOH, reflux, 1 h View Scheme

1: 1.) NaH, 2.) NaOH 2: 75 percent / Na(Hg), disodium hydrogen phosphate / methanol; tetrahydrofuran 3: 1.) BH3*THF, 2.) HCl / 1.) reflux, 1 h, 2.) MeOH, reflux, 1 h View Scheme

1: 75 percent / aq. sodium chloride / dimethylformamide / 3 h / Heating 2: 1.) BH3*THF, 2.) HCl / 1.) reflux, 1 h, 2.) MeOH, reflux, 1 h View Scheme

1: 75 percent / CH2Cl2 / 5 h / Ambient temperature 2: 91 percent / Et3N, DMAP / ethyl acetate / 1 h / 0 °C 3: Mn(OAc)3*2H2O, Cu(OAc)2*H2O / acetic acid / 12 h / Ambient temperature 4: 77 percent / aq. NaCl / dimethylformamide / 3 h / Heating 5: 1.) 9-BBN, 2.) 30percent aq. H2O2, 2 M aq. NaOH / 1.) THF, 20 deg C, overnight, 2.) THF, 12 h 6: pyridinium dichromate / dimethylformamide / 1 h / Ambient temperature 7: methanol; diethyl ether 8: 56 percent / BH3*THF / tetrahydrofuran / 1 h / Heating View Scheme