Water → HCID 178484843, compound

Participants

Reaction Steps

Over a period of 6 h to a suspension of 37.9 g (0.94 mol, 2.0 eq) of LAH in 1.3 L of THF was added a suspension of 117 g (0.47 mol) of trans-4-hydroxy-cyclohexylcarbamic acid benzyl ester in 1 L of THF 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 triturated with n-hexane to yield 27.9 g (46%) of trans-4-methylamino-cyclohexanol. Column chromatography of the mother liquor on silica gel yielded additional 17.1 g (28%) of trans-4-methylamino-cyclohexanol as white solid, MS: 129 (MH+) [in analogy to: Venuti et al., J.Med.Chem. 30:303-318 (1987)].

Provenance & Evidence