반응 #53812

반응 방정식

LAH

trans-4-Hydroxy-cyclohexylcarbamic acid benzyl ester

Na2SO4

water

→

trans-4-Methylamino-cyclohexanol

수율 46.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타between 5-10° C
3. 3
   온도The reaction was refluxed over night
4. 4
   workup.ADDITIONwas added
5. 5
   여과filtered
6. 6
   농축concentrated

실험 절차

To a suspension of 37.9 g (0.94 mol, 2.0 eq) LAH in 1.3 l THF was added a suspension of 117 g (0.47 mol) trans-4-Hydroxy-cyclohexylcarbamic acid benzyl ester in 11 THF over a period of 6 h via a cannula keeping the temperature between 5-10° C. The reaction was refluxed over night and a mixture of Na2SO4, silica gel and water (160 g, 50 g, 80 ml) was added, stirred for additional 30 min, filtered and concentrated. The crude material was titurated with hexane to yield 27.9 g (46%) trans-4-Methylamino-cyclohexanol. Column chromatography of the mother liquor on silica gel yielded additional 17.1 g (28%) trans-4-Methylamino-cyclohexanol as white solid, MS: 129 (MH+) (in analogy to Venuti, Michael C.; Jones, Gordon H.; Alvarez, Robert; Bruno, John J.; J.Med.Chem.; 30; 2; 1987; 303-318).

출처