Multi-step reaction with 6 steps
1: 78 percent / 2 M NaOH / toluene / 48 h / 25 °C
2: 1) diisopropylethylamine, 2) benzyl alcohol / 1) THF, 25 deg C, 18 h, 2) THF, 25 deg C, 4 h
3: 1) 1H-tetrazole, 2) m-chloroperoxybenzoic acid / 1) CH2Cl2, 25 deg C, 8 h, 2) -78 deg C to 25 deg C, overnight
4: 88percent HCOOH, H2O / tetrahydrofuran / 0.5 h / 25 °C
5: 1) 1H-tetrazole, 2) m-chloroperoxybenzoic acid / 1) CH2Cl2, 25 deg C, 1 h, 2) -78 deg C to 25 deg C, overnight
6: H2 / Pd(OH)2-C / acetic acid / 6 h / 760 Torr
With
1H-tetrazole; sodium hydroxide; formic acid; water; hydrogen; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; benzyl alcohol;
palladium hydroxide - carbon;
In
tetrahydrofuran; acetic acid; toluene;
DOI:10.1016/S0008-6215(00)90513-5