Reacción #72015

Ecuación de reacción

tert-butyl 3-isopropoxy-4-oxopiperidine-1-carboxylate

tert-Butyl 3-isopropoxy-4-oxopiperidine-1-carboxylate

Benzylamine

sodium (triacetoxy)borohydride

→

title compound

tert-Butyl cis(±)-4-(benzylamino)-3-isopropoxypiperidine-1-carboxylate

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction solution was concentrated under reduced pressure
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   Lavadowashed with saturated aqueous sodium bicarbonate solution and brine
4. 4
   Secadodried over magnesium sulfate
5. 5
   Concentraciónconcentration under reduced pressure
6. 6
   Otrothe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate)

Procedimiento

A solution of tert-butyl 3-isopropoxy-4-oxopiperidine-1-carboxylate obtained in Example (147c) (105 mg, 0.408 mmol) in 1,2-dichloroethane (2 mL) was cooled in an ice water bath. Benzylamine (87.6 μL) and sodium (triacetoxy)borohydride (212 mg, 1.0 mmol) were added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine, and dried over magnesium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate) to obtain 120 mg of the title compound as a colorless oily substance (85%).

Fuente