Benzylamine → (1R,2R)-2-(benzylamino)cyclohexanol

Participants

Reaction Steps

A mixture of cyclohexene oxide (1) (19 mL, 0.2 mol, Aldrich cat #C10, 280-4) and benzylamine (27) (21 mL, 0.2 mol, Aldrich cat #407712) in water (5 mL) was refluxed for 3 hours. The cooled reaction mixture was partitioned between 4M aq NaOH (100 mL) and methyl t-butyl ether (150 mL). The aqueous layer was further extracted with methyl t-butyl ether (2×100 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give trans-2-benzylaminocyclohexan-1-ol (28) as a low melting point solid (39.4 g, 96% yield);

Provenance & Evidence