Réaction #2182657

Équation de réaction

(S)-1-benzyl-5-methyl-piperidin-3-one

K-selectride

→

titled product

Rendement 87.7%

(3S,5S)-1-Benzyl-5-methyl-piperidin-3-ol

Rendement 87.7%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autreto reach room temperature
2. 2
   Autrethe tetrahydrofuran removed by evaporation
3. 3
   workup.DISSOLUTIONthe residue the residue redissolved in dichloromethane
4. 4
   Lavagewashed with sat. aq. sodium hydrogencarbonate solution
5. 5
   Séchagedried (Na2SO4)
6. 6
   Concentrationconcentrated
7. 7
   AutrePurification by flash column chromatography (ethyl acetate/heptane 1:4)

Mode opératoire

To a solution of (S)-1-benzyl-5-methyl-piperidin-3-one (1.1 g, 5 mmol) in dry tetrahydrofuran (15 ml) at −78° C. was added K-selectride (10.8 ml, 11 mmol, 1 M solution in tetrahydrofuran). After 2 h at −78° C. a few drops of water were cautiously added, the reaction allowed to reach room temperature, the tetrahydrofuran removed by evaporation and the residue the residue redissolved in dichloromethane, washed with sat. aq. sodium hydrogencarbonate solution, dried (Na2SO4) and concentrated. Purification by flash column chromatography (ethyl acetate/heptane 1:4) afforded the titled product as a crystalline solid (0.9 g, 43%). MS (ISP)=204.3 (M+H)+.

Source