Reaction #89107

Reaction equation

LAH

ethyl 5,5-diethoxypiperidine-2-carboxylate

→

rac-(5,5-diethoxypiperidin-2-yl)methanol

Yield 95.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled down to 0° C.
2. 2
   Otherquenched sequentially with water (0.47 g), 15% NaOH (0.47 g) and water (1.41 g)
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate was concentrated in vacuo

Procedure

A suspension of LAH (0.47 g, 12.25 mmol) in anhydrous THF (5 mL) was added a solution of ethyl 5,5-diethoxypiperidine-2-carboxylate (0.6 g, 2.45 mmol) in anhydrous THF (5 mL) dropwise at rt. The resulting mixture was refluxed at 70° C. for overnight. The reaction mixture was cooled down to 0° C. and quenched sequentially with water (0.47 g), 15% NaOH (0.47 g) and water (1.41 g). The resulting suspension was stirred at rt for 1 h and filtered. The filtrate was concentrated in vacuo to give desired rac-(5,5-diethoxypiperidin-2-yl)methanol in 95% yield as colorless oil. 1H NMR (CDCl3, 400 MHz) δ 3.54-3.32 (m, 6H), 3.11-3.04 (m, 1H), 2.56-2.46 (m, 2H), 2.05-2.00 (m, 1H), 1.52-1.23 (m, 3H), 1.15-1.07 (m, 6H).

Source