11-Cyclopropyl-5,11-dihydro-4-(hydroxyMethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4] diazepin-6-one synthesis

Yield:-

Steps:

Multi-step reaction with 9 steps
1.1: 71 percent / N-chlorosuccinimide / CH₂Cl₂ / 1 h / 0 - 5 °C
2.1: 56 percent / 2-t-butyl-4-methylphenol / toluene / 2 h / 90 - 95 °C
3.1: 49 percent / sodium carbonate / toluene / 2 h / 90 - 100 °C
4.1: 83.6 percent / xylene / 72 h / 105 °C
5.1: 54 percent / sodium hydride; pyridine / 1 h / 75 - 85 °C
6.1: trifluoroacetic acid / 168 h
7.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
7.2: tetrahydrofuran / 1 h / 20 °C
8.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
9.1: ozone / methanol / 0.17 h / -40 °C
9.2: methyl sulfide / methanol
9.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C

References:

Grozinger, Karl G.;Byrne, Denis P.;Nummy, Laurence J.;Ridges, Michael D.;Salvagno, Annette [Journal of Heterocyclic Chemistry,2000,vol. 37,# 2,p. 229 - 239]