Multi-step reaction with 12 steps
1.1: Et3N; molecular sieves 4A / CH2Cl2 / 20 °C
2.1: 55.10 g / ethanol; H2O / 2 h / Heating
3.1: 98 percent / aq. HCl / 72 h / Heating
4.1: DCC / dimethylformamide / 2 h / 20 °C
5.1: Et3N / dimethylformamide / 20 °C
6.1: 3.40 g / acetic anhydride; NaOAc / 2 h / Heating
7.1: NaBH4 / methanol / 0 - 20 °C
7.2: NaBH4; TFA / 0 - 20 °C
7.3: 792 mg / acetonitrile; CH2Cl2 / 20 °C
8.1: 74 percent / aq. NH4OAc; Cd-Pb couple / tetrahydrofuran / 20 °C
9.1: 92 percent / Et3N / CH2Cl2 / 9 h / 20 °C
10.1: H2S (gas); Et3N; pyridine / 20 °C
11.1: acetone / 20 °C
12.1: NH4OAc / methanol / 20 °C
With
pyridine; hydrogenchloride; sodium tetrahydroborate; 10% Cd/Pd; 4 A molecular sieve; hydrogen sulfide; ammonium acetate; sodium acetate; acetic anhydride; triethylamine; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
1.1: Knoevenagel condensation;
DOI:10.1021/jm030354b