Multi-step reaction with 12 steps
1.1: 765 mg / KHCO3 / dimethylformamide / 12 h / 20 °C
2.1: 59 percent / SnCl4 / CH2Cl2 / 1 h / -19 °C
3.1: 74 percent / NaOBn / phenylmethanol / 1 h / 0 °C / pH 11
4.1: (Bu3Sn)2O / toluene / 2 h / Heating
4.2: 66 percent / toluene / 72 h / 20 °C
5.1: 145 mg / pyridine / 4 h / 20 °C
6.1: 92 percent / 18-crown-6 / benzene / 4 h / 20 °C
7.1: 96 percent / tetrabutylammonium azide / hexane / 20 °C / ultrasonication
8.1: H2 / Pd/C / benzene / 1 h
9.1: 311 mg / 0.5 h / 20 °C
10.1: 91 percent / H2 / Pd(OH)2 / ethanol / 1 h
11.1: 81 percent / WSC / CH2Cl2 / 1 h / 0 °C
12.1: 333 mg / NaOMe / methanol / 2 h / pH 10
With
pyridine; 18-crown-6 ether; hydrogen; sodium methylate; tetrabutylammoniun azide; tin(IV) chloride; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium phenyl-methanolate; bis(tri-n-butyltin)oxide;
palladium dihydroxide; palladium on activated charcoal;
In
methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzyl alcohol; benzene;
DOI:10.1081/CAR-100103953