1-Aminocyclohexanecarboxylic acid → (1-Aminocyclohexyl)methanol

Participants

Reaction Conditions

Reaction Steps

LiAlH4 powder (2.28 g, 60.0 mmol) was placed in a 200 mL round-bottom flask equipped with a magnetic stir bar. The flask was evacuated and backflushed with Ar, cooled to 0° C., and charged with dry THF (10 mL) via cannula. 1-Amino-cyclohexylcarboxylic acid (2.86 g, 20.0 mmol) was added in small portions as a solid. Upon completion of the addition, the mixture was heated to reflux for 12 h. The mixture was cooled to 0° C., treated slowly with satd aq Na2 CO3 (50 mL), warmed to rt, and stirred for 2 h. A white precipitate formed, which was separated by filtration, washed with THF (75 mL), and washed twice with EtOAc (100 mL). The filtrate was concentrated in vacuo. The residue was dissolved in DCM (50 mL), dried over Na2 SO4, and concentrated in vacuo to afford 2.80 g (97%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 3.33 (s, 2H), 1.45-1.56 (m, 6H), 1.31-1.45 (m, 4H).

Provenance & Evidence