Multi-step reaction with 12 steps
1.1: ethyl chloroformate / tetrahydrofuran / 0.25 h / -10 - 0 °C
1.2: 83 percent / NaBH4 / tetrahydrofuran; methanol / 0 °C
2.1: 80 percent / triethylamine / CH2Cl2 / 1.5 h / 0 - 20 °C
3.1: 69 percent / Cs2CO3 / dimethylformamide / 0 °C
4.1: sulfuryl chloride; acetic anhydride / CH2Cl2 / 1 h / -20 - -5 °C
5.1: 73 percent / NH3 / CH2Cl2 / 0.25 h / -10 °C
6.1: 85 percent / NaIO4 / RuCl3*H2O / CH2Cl2; acetonitrile; H2O / 0.75 h / 0 - 20 °C
7.1: hydrogen / 10percent Pd/C / ethanol / 4 h
8.1: 230 mg / tetrahydrofuran
9.1: TFA / CH2Cl2 / 0.5 h / 0 °C
10.1: 81 mg / BOP; DIPEA / CH2Cl2
11.1: TFA / CH2Cl2 / 0.5 h / 0 °C
12.1: 68 mg / BOP; DIPEA / CH2Cl2
With
sodium periodate; sulfuryl dichloride; ammonia; hydrogen; chloroformic acid ethyl ester; acetic anhydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
ruthenium trichloride;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
1.1: Substitution / 1.2: Reduction / 2.1: Substitution / 3.1: Substitution / 4.1: Deacetylation / 5.1: Substitution / 6.1: Oxidation / 7.1: Hydrogenolysis / 8.1: Substitution / 9.1: Hydrolysis / 10.1: Condensation / 11.1: Hydrolysis / 12.1: Condensation;
DOI:10.1002/1099-0690(200004)2000:7<1219::AID-EJOC1219>3.0.CO;2-P