反应详情

温度

5 °C

Sodium triacetoxyborohydride (3.1 g, 14.6 mmol, 3 equiv) is added to a cold (5° C.) solution of 4-(4-nitro-phenyl)-piperidine (1 g, 4.9 mmol) and acetaldehyde (0.82 mL, 14.6 mmol, 3 equiv) in DCM (20 mL). The reaction mixture is stirred for 1 h at 5° C. and then diluted with DCM and a saturated aqueous solution of NaHCO3. The layers are separated and the aqueous layer is extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 98:2) to provide the title compound as a yellow oil. ESI-MS: 235.1 [MH]+; tR=2.64 min (purity: 85%, system 1); TLC: Rf=0.14 (DCM/MeOH+1% NH3aq, 98:2).

1. customThe layers are separated
2. extractionthe aqueous layer is extracted with DCM
3. washThe organic phase is washed with brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 98:2)