Multi-step reaction with 11 steps
1.1: diisopropylamine / Pd(PPh3)4 / tetrahydrofuran / 0.33 h / 20 °C
1.2: 99 percent / CuI / tetrahydrofuran / 12 h
2.1: 99 percent / LAH / tetrahydrofuran / 20 h / Heating
3.1: 95 percent / imidazole / dimethylformamide / 0 - 20 °C
4.1: 72 percent / m-CPBA; NaOAc / CH2Cl2 / 6 h / 20 °C
5.1: 71 percent / CuI / tetrahydrofuran / 6 h / 20 °C
6.1: 40 percent / sodium hydride / dimethylformamide / 5 h / 20 °C
7.1: 89 percent / acetic acid / tetrahydrofuran; H2O
8.1: methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C
8.2: 92 percent / NaI / acetone / 1.5 h / Heating
9.1: 56 percent / potassium carbonate / acetone / 22 h / Heating
10.1: 58 percent / formaldehyde; K2CO3 / dioxane; H2O / 12 h / 35 °C
11.1: 71 percent / trans-1,2-(diamino)cyclohexane; SnCl4; bis(trimethylsilyl)peroxide / CH2Cl2 / 40 h / 20 °C
With
1H-imidazole; lithium aluminium tetrahydride; formaldehyd; bis-trimethylsilanyl peroxide; sodium acetate; tin(IV) chloride; sodium hydride; potassium carbonate; acetic acid; rac-diaminocyclohexane; methanesulfonyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja029139v