Multi-step reaction with 8 steps
1: 97 percent / BH3*SMe2 / diethyl ether
2: 96 percent / imidazole, DMAP / CH2Cl2 / 1 h / 0 °C
3: 90 percent / LiAlH4 / diethyl ether / 15 h / 0 °C
4: 91 percent / NaHCO3, NaCl / dimethylformamide / 1.) r.t., 30 min, 2.) r.t., 16 h
5: 87 percent / TBAF*3H2O / tetrahydrofuran / 12 h / Ambient temperature
6: 1.) oxalyl chloride, DMSO, 2.) N-methylmorpholine / 1.) CH2Cl2, -50 deg C, 2 min, 2.) CH2Cl2, -55 to 50 deg C, 20 min
7: 1.) tin(II) triflate, N-ethylpiperidine / 1.) CH2Cl2, -45 deg C, 3 h, 2.) CH2Cl2, -80 deg C, 20 min
8: 82 percent / NaBH4, H2O / tetrahydrofuran / 1.5 h
With
1-ethyl-piperidine; 4-methyl-morpholine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; tin(II) trifluoromethanesulfonate; oxalyl dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; dimethyl sulfoxide; sodium chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;