Potassium;tri(butan-2-yl)boranuide → (3SR,4SR)-1,4-dibenzyl-piperidin-3-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 9.0 g (SR)-1,4-dibenzyl-piperidin-3-one (32 mmol) in 200 ml dry THF were added at −78° C. dropwise 48 ml K-selectride® (1 N in THF, 48 mmol). The reaction mixture was stirred for 1 h at −70° C. and then warmed to r.t. The reaction was quenched by the addition of 100 ml NaHCO3-solution and the aqueous phase was extracted twice with ethyl acetate (200 ml). The combined organic phases were washed with water (100 ml) and brine (100 ml). The organic phase was dried over MgSO4, filtrated and the solvent was removed under reduced pressure to give the crude product. Purification by chromatography (ethyl acetate/hexane 1/2 to 2/1) yielded 6.5 g of the product (23 mmol, 72%) as a yellow oil.

Provenance & Evidence