Multi-step reaction with 7 steps
1: 58 percent / piperidinium acetate / benzene / Heating
2: 72 percent / lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C
3: 14.06 g / LiAlH4 / diethyl ether / a.) 0 deg C, 10 min, b.) room temperature, 3.5 h
4: 83 percent / Et3N, DMAP / CH2Cl2 / 20 h / Ambient temperature
5: H2O; propan-2-ol / pig pancreatic lipase, pH 7 buffer (K2HPO4-KH2PO4)
6: 1.) diisopropylethylamine, 2.) KOH / 1.) CH2Cl2, room temperature, 2.) MeOH
With
dmap; potassium hydroxide; lithium aluminium tetrahydride; piperdinium acetate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; isopropyl alcohol; benzene;
DOI:10.1021/jo00031a039