Water → trans-(2-Aminocyclohexyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of LiAlH4 (796 mg, 20.97 mmol) in anhydrous THF (20 mL) at rt was added portion-wise (1R,2R)-2-aminocyclohexanecarboxylic acid (1 g, 6.99 mmol). The mixture was heated at 80° C. for 4 h before it was cooled to 0° C. Water (1 mL), 1M aq NaOH (1 mL), and water (3 mL) were added sequentially. The mixture was filtered and the filtrate partitioned between a mixture of DCM, 1M aq NaOH, and saturated aq sodium potassium tartrate. The organic layer was separated and washed with 1M aq NaOH. The organic layer was separated, dried over MgSO4, filtered, and under reduced pressure to afford ((1R,2R)-2-aminocyclohexyl)methanol (180 mg) which was not purified further. LCMS (ESI) m/z 130 (M+H)+.

Provenance & Evidence