trifluoroacetic acid in dichloromethane 1 h; Ambient temperature;

1: 96 percent / CH2Cl2 / 68 h / Ambient temperature 2: 95 percent / H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 3: 100 percent / methanol / 12 h / Ambient temperature 4: 85 percent / CH2Cl2 / 1.5 h / Ambient temperature 5: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 6: methanol / 12 h / Ambient temperature 7: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 8: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 3 h, 2.) RT, 12 h 9: 1.) 85percent 3-chloroperoxybenzoic acid, 2.) NaBH3CN / 1.) acetone, 0 deg C, 30 min, 2.) acetic acid, 12 h 10: 95 percent / trifluoroacetc acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 100 percent / methanol / 12 h / Ambient temperature 2: 85 percent / CH2Cl2 / 1.5 h / Ambient temperature 3: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 4: methanol / 12 h / Ambient temperature 5: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 6: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 3 h, 2.) RT, 12 h 7: 1.) 85percent 3-chloroperoxybenzoic acid, 2.) NaBH3CN / 1.) acetone, 0 deg C, 30 min, 2.) acetic acid, 12 h 8: 95 percent / trifluoroacetc acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 95 percent / H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 2: 100 percent / methanol / 12 h / Ambient temperature 3: 85 percent / CH2Cl2 / 1.5 h / Ambient temperature 4: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 5: methanol / 12 h / Ambient temperature 6: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 7: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 3 h, 2.) RT, 12 h 8: 1.) 85percent 3-chloroperoxybenzoic acid, 2.) NaBH3CN / 1.) acetone, 0 deg C, 30 min, 2.) acetic acid, 12 h 9: 95 percent / trifluoroacetc acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 85 percent / CH2Cl2 / 1.5 h / Ambient temperature 2: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 3: methanol / 12 h / Ambient temperature 4: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 5: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 3 h, 2.) RT, 12 h 6: 1.) 85percent 3-chloroperoxybenzoic acid, 2.) NaBH3CN / 1.) acetone, 0 deg C, 30 min, 2.) acetic acid, 12 h 7: 95 percent / trifluoroacetc acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: methanol / 12 h / Ambient temperature 2: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 3: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 3 h, 2.) RT, 12 h 4: 1.) 85percent 3-chloroperoxybenzoic acid, 2.) NaBH3CN / 1.) acetone, 0 deg C, 30 min, 2.) acetic acid, 12 h 5: 95 percent / trifluoroacetc acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 2: methanol / 12 h / Ambient temperature 3: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 4: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 3 h, 2.) RT, 12 h 5: 1.) 85percent 3-chloroperoxybenzoic acid, 2.) NaBH3CN / 1.) acetone, 0 deg C, 30 min, 2.) acetic acid, 12 h 6: 95 percent / trifluoroacetc acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: H2 / Pd(OH)2/C / acetic acid / 2 h / 2585.7 Torr 2: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 3 h, 2.) RT, 12 h 3: 1.) 85percent 3-chloroperoxybenzoic acid, 2.) NaBH3CN / 1.) acetone, 0 deg C, 30 min, 2.) acetic acid, 12 h 4: 95 percent / trifluoroacetc acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1.1: Et3N / CH2Cl2 / 0.05 h / 20 °C 2.1: 95 percent / Et3N; DMAP / CH2Cl2 / 0.17 h / 20 °C 3.1: 80 percent / Cs2CO3; nBu4NI / acetonitrile / 1.5 h / 60 °C 4.1: 98 percent / Et3N; DMAP / CH2Cl2 / 1 h / 20 °C 5.1: 97 percent / Cs2CO3; thiophenol / acetonitrile / 10 h / 20 °C 6.1: 93 percent / ethanol / 24 h / 60 °C 7.1: 98 percent / ammonium fluoride / acetonitrile / 10 h / 60 °C 8.1: 90 percent / Ph3P; DEAD / CH2Cl2; benzene; toluene / 0.17 h / 20 °C 9.1: m-CPBA / CH2Cl2 / 1 h / -10 °C 9.2: 90 percent / Me2S / CH2Cl2 / -10 - 20 °C 10.1: 95 percent / SOCl2 / CH2Cl2; methanol / 2.5 h / 20 °C 11.1: 4(chlorodiphenylmethyl)phenoxymethylated polystyrene polymer; iPr2NEt / CH2Cl2 / 24 h / 20 °C 11.2: 2-mercaptoethanol; DBU / dimethylformamide / 26 h / 20 °C 11.3: TFA / CH2Cl2 / 0.08 h / 20 °C View Scheme

1: 91 percent / 4-(N,N-dimethylamino)pyridine / acetonitrile / 0.25 h 2: 48 percent / sodium 2-ethylhexanoate, triphenylphosphine, tetrakis(triphenylphosphine)palldium / CH2Cl2; ethyl acetate / 1 h 3: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 3 h, 2.) RT, 12 h 4: 1.) 85percent 3-chloroperoxybenzoic acid, 2.) NaBH3CN / 1.) acetone, 0 deg C, 30 min, 2.) acetic acid, 12 h 5: 95 percent / trifluoroacetc acid / CH2Cl2 / 1 h / Ambient temperature View Scheme