Multi-step reaction with 11 steps
1: 99 percent / LiAlH4 / diethyl ether / 0.08 h / 0 deg C to r.t.
2: 98 percent / pyridine / Ambient temperature
3: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 6 h / Ambient temperature
4: 98 percent / d-camphorsulfonic acid / benzene / 0.5 h / Ambient temperature
5: 96 percent / LiAlH4 / diethyl ether / 1 h / 0 deg C to r.t.
6: 96 percent / pyridine / 2 h / Ambient temperature
7: 94 percent / NaI / acetone / 8 h / Heating
8: 93 percent / dimethylformamide / 6 h / 60 °C
9: 1) n-BuLi / 1) Et2O, hexane, 15 min, r.t., 2) Et2O, hexane, -75 deg C, 2 h
10: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 1 h, 2) 3 h
11: 84 percent / Al-Hg / tetrahydrofuran; H2O / 3 h / Ambient temperature
With
pyridine; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; aluminium amalgam; (1S)-10-camphorsulfonic acid; hydrogen; dimethyl sulfoxide; triethylamine; sodium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4020(01)87185-4