Multi-step reaction with 7 steps
1: aq. NaHCO3, 1 N aq. NaOH / tetrahydrofuran / Ambient temperature
2: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 10 min
3: 1.) AcOH, 2.) sodium cyanoborohydride / 1.) CH3CN, RT, 20 min, 2.) CH3CN, RT, overnight
4: K2CO3 / methanol; H2O / 3 h / Heating
5: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / Ambient temperature
6: 70 percent / H2 / 10percent Pd/C / ethanol / 16 h / 760 Torr
7: 65 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / Ambient temperature
With
sodium hydroxide; oxalyl dichloride; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1021/jm00037a005