Multi-step reaction with 6 steps
1: 70 percent / NaH / tetrahydrofuran / a.) 0 deg C, 2 h, b.) room temperature, 3 h, c.) 40 deg C, 3 h
2: 17.20 g / LiAlH4 / diethyl ether / a.) 0 deg C, 30 min, b.) room temperature, 5.5 h
3: 72 percent / pyridine / 4 h / 0 °C
4: 75 percent / H2O; propan-2-ol / pig pancreatic lipase, pH 7 buffer (K2HPO4-KH2PO4)
5: 1.) imidazole, 2.) KOH / 1.) DMF, room temperature, 2.) MeOH, a.) 0 deg C, b.) room temperature
6: 82 percent / EtN(iPr)2 / CH2Cl2 / a.) 0 deg C, b.) room temperature
With
pyridine; 1H-imidazole; potassium hydroxide; lithium aluminium tetrahydride; sodium hydride; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; isopropyl alcohol;
DOI:10.1021/jo00031a039