Imidazole → Tert-butyl 3-(iodomethyl)piperidine-1-carboxylate

Imidazole (1.58 g, 23.2 mmol), triphenylphosphine (6.09 g, 23.2 mmol) and iodine (4.72 g, 18.6 mmol) were added to 1-(tert-butoxycarbonyl)piperidin-3-yl methanol (2.00 g, 9.29 mmol) in benzene (50 mL). The mixture was stirred at room temperature for 3 hours. Subsequently, the reaction mixture was filtered through Celite and the solvent was evaporated. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 2.91 g (96%) of the desired compound as a pale yellow oil.

1. filtrationSubsequently, the reaction mixture was filtered through Celite
2. customthe solvent was evaporated
3. additionWater was added to the residue
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with brine
6. dry with materialwas dried over magnesium sulfate
7. customfollowed by evaporation of the solvent
8. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

ORD-Eintrag

ord-5b4128e737e94f5e9ffb97cc5e691afa

Quelldatensatz

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07902367B2