Multi-step reaction with 9 steps
1: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h
2: LiAlH4 / diethyl ether / 3 h / Ambient temperature
3: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature
4: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C
6: concd. NH4OH / acetone / 1.5 h
7: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature
8: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d
9: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min
With
hydrogenchloride; ammonium hydroxide; lithium aluminium tetrahydride; 4 A molecular sieve; DBN; sodium cyanoborohydride; toluene-4-sulfonic acid; pyridinium chlorochromate; trimethyl orthoformate;
In
methanol; diethyl ether; dichloromethane; acetone; toluene;
DOI:10.1021/jm00110a008